Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: An efficient approach to 1<i>H</i>-pyrazolo[1,2-<i>b</i>]phthalazine-5,10-diones

Hassan Kefayati; Shadi Homayoon Amlashi; Reyhaneh Kazemi-Rad; Adeleh Delafrooz

doi:10.1016/j.crci.2013.09.017

Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: An efficient approach to 1H-pyrazolo[1,2-b]phthalazine-5,10-diones

Hassan Kefayati ¹ ; Shadi Homayoon Amlashi ² ; Reyhaneh Kazemi-Rad ³ ; Adeleh Delafrooz ²

¹ Department of Chemistry, Guilan Science and Research Branch, Islamic Azad University, Rasht, Iran
² Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran
³ Young Researchers and Elite Club, Guilan Science and Research Branch, Islamic Azad University, Rasht, Iran

Comptes Rendus. Chimie, Volume 17 (2014) no. 9, pp. 894-898.

Résumé

Electrocatalytic multicomponent transformation of phthalhydrazide, aromatic aldehydes and malononitrile in n-propanol in an undivided cell in the presence of sodium bromide as an electrolyte leads to 1H-pyrazolo[1,2-b]phthalazine-5,10-diones in short reaction times (4–8 min) and high yields (85–98%) at room temperature. The developed efficient electrocatalytic approach to the corresponding 1H-pyrazolo[1,2-b]phthalazine-5,10-diones is beneficial from the viewpoint of diversity-oriented large-scale processes and represents a new example of the ecologically pure synthetic concept for electrocatalytic multicomponent reactions strategy.

Métadonnées

Reçu le : 2013-07-12
Accepté le : 2013-09-30
Publié le : 2014-02-18

DOI : 10.1016/j.crci.2013.09.017

Mots-clés : Electrocatalytic transformation, Electrogenerated base, Pyrazolo[1, 2-b]phthalazine-5, 10-dione, Phthalhydrazide, Multicomponent reaction

Affiliations des auteurs :

Hassan Kefayati ¹ ; Shadi Homayoon Amlashi ² ; Reyhaneh Kazemi-Rad ³ ; Adeleh Delafrooz ²

¹ Department of Chemistry, Guilan Science and Research Branch, Islamic Azad University, Rasht, Iran
² Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran
³ Young Researchers and Elite Club, Guilan Science and Research Branch, Islamic Azad University, Rasht, Iran

@article{CRCHIM_2014__17_9_894_0,
     author = {Hassan Kefayati and Shadi Homayoon Amlashi and Reyhaneh Kazemi-Rad and Adeleh Delafrooz},
     title = {Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: {An} efficient approach to {1\protect\emph{H}-pyrazolo[1,2-\protect\emph{b}]phthalazine-5,10-diones}},
     journal = {Comptes Rendus. Chimie},
     pages = {894--898},
     publisher = {Elsevier},
     volume = {17},
     number = {9},
     year = {2014},
     doi = {10.1016/j.crci.2013.09.017},
     language = {en},
}

TY  - JOUR
AU  - Hassan Kefayati
AU  - Shadi Homayoon Amlashi
AU  - Reyhaneh Kazemi-Rad
AU  - Adeleh Delafrooz
TI  - Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: An efficient approach to 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
JO  - Comptes Rendus. Chimie
PY  - 2014
SP  - 894
EP  - 898
VL  - 17
IS  - 9
PB  - Elsevier
DO  - 10.1016/j.crci.2013.09.017
LA  - en
ID  - CRCHIM_2014__17_9_894_0
ER  -

%0 Journal Article
%A Hassan Kefayati
%A Shadi Homayoon Amlashi
%A Reyhaneh Kazemi-Rad
%A Adeleh Delafrooz
%T Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: An efficient approach to 1H-pyrazolo[1,2-b]phthalazine-5,10-diones
%J Comptes Rendus. Chimie
%D 2014
%P 894-898
%V 17
%N 9
%I Elsevier
%R 10.1016/j.crci.2013.09.017
%G en
%F CRCHIM_2014__17_9_894_0

Hassan Kefayati; Shadi Homayoon Amlashi; Reyhaneh Kazemi-Rad; Adeleh Delafrooz. Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: An efficient approach to 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Comptes Rendus. Chimie, Volume 17 (2014) no. 9, pp. 894-898. doi : 10.1016/j.crci.2013.09.017. https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2013.09.017/

Version originale du texte intégral

Le texte intégral ci-dessous peut contenir quelques erreurs de conversion par rapport à la version officielle de l'article publié.

1 Introduction

Pyrazoles are an important class of compounds for new drugs’ development, as they are the core structure of numerous biologically active compounds, including blockbuster drugs such as celecoxib, Viagra, pyrazofurine, and many others [1–4]. Furthermore, heterocycles containing a phthalazine moiety are of current interest due to their pharmacological and biological activities [5–7]. For example, 1H-pyrazolo[1,2-b]phthalazine-dione is described as an anti-inflammatory, analgesic, anti-hypoxic, and anti-pyretic agent [6]. Phthalazine derivatives are also found to possess anti-convulsant [8], cardiotonic [9], and vasorelaxant [10] activities.

To our knowledge, there are only a few multicomponent reports for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones [11]. However, in spite of their potential utility, some of the reported synthetic methods suffer from limitations such as the use of an expensive catalyst, long reaction times, difficult work-up and drastic reaction conditions. Therefore, any new facile and highly efficient synthetic approach to corresponding heterocycles containing a phthalazine ring fragment is highly desirable.

Recently, it was found that chemical bases could be replaced with an electrogenerated base (EGB) to promote reactions in higher yields [12]. Electroorganic reactions proceed generally smoothly and take place with good to excellent yields with easy work-up and do not require the use of harsh conditions such as high temperatures and expensive reagents. Also, to date, no reports have been published on the electrosynthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones.

All these facts have prompted us to design a convenient and facile multicomponent synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones based on the electrocatalytic transformation of phthalhydrazide 1, aromatic aldehydes 2a–k, and malononitrile 3 in an undivided cell (Scheme 1).

Scheme 1
Electrosynthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones.

2 Results and discussion

First, to evaluate the synthetic potential of the procedure proposed and to optimize the electrolysis conditions, the electrocatalytic multicomponent transformation of phthalhydrazide 1, 3-nitrobenzaldehydes 2a, and malononitrile 3 into the corresponding 1H-pyrazolo[1,2-b]phthalazine-5,10-dione 4a in n-PrOH in an undivided cell containing an iron electrode as cathode and a Pt electrode as anode at constant current in the presence of sodium bromide as an electrolyte was studied at room temperature. As it is indicated in Table 1, the current density 12 mA/cm² (I = 60 mA, electrode surface 5 cm²) in n-PrOH was found to be the optimum one for the electrochemically induced chain process and afforded the highest yield (98%) of 4a. The current density increase up to 16 mA/cm² (I = 80 mA) results in a slight decrease of the reaction yield, which may be connected with the activation of undesired direct electrochemical processes possible under these conditions and leading to the oligomerization of the starting material.

Entry	Alcohol	I (mA)	Current density (mAcm⁻²)	Time (min)	Electricity passed (F mol⁻¹)	Yield (%)
1	EtOH	30	6	8	0.15	79
2	n-PrOH	30	6	8	0.15	85
3	n-PrOH	50	10	5	0.15	90
4	n-PrOH	60	12	4	0.15	98
5	n-PrOH	80	16	3	0.15	93

^a Phthalhydrazide (1 mmol), 3-nitrobenzaldehyde (1 mmol), malononitrile (1 mmol), NaBr (0.1 mmol), alcohol (10 mL), iron cathode (5 cm²), platinum anode (5 cm²), room temperature.

Under the optimal conditions (current density 12 mA/cm²), the electrolysis of phthalhydrazide 1, aromatic aldehydes 2a–k, and malononitrile 3 in an undivided cell gives rise to the corresponding 1H-pyrazolo[1,2-b]phthalazine-5,10-diones 4a–k in short reaction times (4–8 min) and high yields (Table 2). The electronic nature of the substituent on the aromatic ring showed no particular effect on the conversion.

Product	Aldehyde	Current density (mAcm⁻²)	Time (min)	Electricity passed (F mol⁻¹)	Yield (%)	Mp (°C)	Mp (°C) (lit. [11d])
4a		12	4	0.15	98	269–270	269–271
4b		12	6	0.22	98	267–269	265–267
4c		12	5	0.19	85	228–229	228–229
4d		12	5	0.19	98	275–277	275–276
4e		12	5	0.19	95	259–261	259–260
4f		12	7	0.26	91	249–250	248–251
4g		12	6	0.22	87	259–261	257–259
4h		12	8	0.30	98	272–274	270–272
4i		12	6	0.22	85	267–268	263–264
4j		12	7	0.26	86	266–268	–
4k		12	5	0.19	98	276–278	–

^a Phthalhydrazide (1 mmol), aromatic aldehydes (1 mmol), malononitrile (1 mmol), NaBr (0.1 mmol), alcohol (10 mL), iron cathode (5 cm²), platinum anode (5 cm²), room temperature.

Taking the above results into consideration, the following mechanism for this electrocatalytic chain transformation is proposed. As the initiation step of the catalytic cycle, the deprotonation of an alcohol at the cathode leads to the formation of propioxide anion. The subsequent reaction in solution between propioxide anion and malononitrile gives rise to malononitrile anion (Scheme 2).

Scheme 2
Formation of propioxide anion at the cathode.

Then, Knoevenagel condensation of malononitrile anion with aromatic aldehydes 2a–k takes place in the solution with elimination of hydroxide anion and formation of arylidene malononitrile 5. The subsequent propioxide anion promoted Michael addition of phetalhydrazide 1 to electron-deficient Knoevenagel adduct 5, followed by intramolecular cyclization to the corresponding 1H-pyrazolo[1,2-b] phthalazine-5,10-diones 4a-k (Scheme 3).

Scheme 3
Proposed mechanism for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones 4a–k.

3 Conclusions

In conclusion, the use of an EGB in comparison with conventional chemistry [11] has advantages such as (i) in situ generation of base, (ii) one-pot reaction in excellent yields under milder conditions, (iii) avoidance of polluting or hazardous chemicals or the addition of base or probase; moreover, its work-up procedure is easy.

4 Experimental

4.1 General

All reagents were purchased from Merck and Fluka and used without further purification. The melting points were obtained in open capillary tubes and were measured on an Electrothermal IA 9100 apparatus. IR spectra were recorded on KBr pellets with a Shimadzu FT-IR 8600 spectrophotometer. ¹H and ¹³C NMR spectra were determined with a Bruker DRX-400 Avance instrument at 400 and 100 MHz. Elemental analysis were carried out using a Thermo Finnigan Flash EA 1112 series instrument.

4.2 General procedure for electrochemical synthesis of pyrazolo[1,2-b]phthalazines

A solution of phthalhydrazide (1.0 mmol), various aryl aldehydes (1.0 mmol), and malononitrile (1.0 mmol) and sodium bromide (0.1 mmol) in n-propanol (10 mL) was electrolyzed in an undivided cell equipped with a magnetic stirrer, a platinum anode and an iron cathode at room temperature under a constant current density of 12 mA/cm² (I = 60 mA, electrodes square 5 cm²).

The progress of the reaction was monitored by thin layer chromatography. After completion of the reaction (4–8 minutes), the obtained precipitate was filtered, and the filter cake was washed with ethanol to yield pure products (4a–k).

4.2.1 3-Amino-1-(4-nitrophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile (4c)

Yellow powder; yield: 85%; mp = 228–229 °C; ¹H NMR (400 MHz, DMSO-d₆): δ_H 8.27–8.29 (m, 1H), 8.22 (d, J = 8.6 Hz, 2H), 8.20 (brs, 2H, NH₂), 8.08–8.10 (m, 1H), 7.97–7.99 (m, 2H), 7.81 (d, J = 8.6 Hz, 2H), 6.30 (s, 1H) ppm; ¹³C NMR (100 MHz, DMSO-d₆): 157.2, 154.2, 151.4, 151.3, 147.8, 146.3, 135.1, 134.3, 129.4, 128.9, 128.5, 127.8, 127.2, 124.2, 116.3, 62.8 ppm; IR (KBr): υ = 3433, 3321, 3076, 2160, 1658, 1558, 1515 cm⁻¹.

4.2.2 3-Amino-1-(2-methoxyphenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile (4e)

Yellow powder; yield: 95%; mp = 259–261 °C; ¹H NMR (400 MHz, DMSO-d₆): δ_H 8.30–8.27 (m, 1H), 8.11–8.09 (m, 1H), 8.02 (brs, 2H, NH₂), 8.01–7.97 (m, 2H), 7.32–7.27 (m, 2H), 7.04 (d, J = 7.6 Hz, 1H), 6.91 (dt, J = 7.6, 0.8 Hz, 1H), 6.35 (s, 1H), 3.74 (s, 3H, OCH₃) ppm; ¹³C NMR (100 MHz, DMSO-d₆): 157.1, 156.9, 153.7, 151.5, 135.2, 134.2, 129.8, 129.1, 129.0, 127.9, 127.8, 127.2, 126.3, 121.2, 116.5, 112.1, 61.1, 59.4, 56.3 ppm; IR (KBr): υ = 3380, 3250, 3184, 2199, 1657, 1564, 1379 cm⁻¹.

4.2.3 3-Amino-1-(3-methoxyphenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b] phthalazine-2-carbonitrile (4f)

Yellow powder; yield: 91%; mp = 249–250 °C; ¹H NMR (400 MHz, DMSO-d₆): δ_H 8.25–8.27 (m, 1H), 8.08–8.10 (m, 3H, NH₂, H), 7.95–7.99 (m, 2H), 7.28 (t, J = 7.6 Hz, 1H), 6.99–7.01 (m, 2H), 6.89 (dd, J = 8.0, 1.6 Hz, 1H), 6.10 (s, 1H), 3.74 (s, 3H, OCH₃) ppm; ¹³C NMR (100 MHz, DMSO-d₆): 159.8, 157.1, 154.1, 151.1 138.1, 134.2, 130.1, 129.5, 129.3, 129.1, 127.3, 127.1, 124.2, 119.2, 113.8, 113.1, 64.0, 55.6 ppm; IR (KBr): υ = 3361, 3259, 3056, 2190, 1654, 1566 cm⁻¹.

4.2.4 3-Amino-1-(2-chlorophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile (4g)

Yellow powder; yield: 87%; mp = 259–261 °C; ¹H NMR (400 MHz, DMSO-d₆): δ_H 8.29–8.27 (m, 1H), 8.14 (brs, 2H, NH₂), 8.11–8.07 (m, 1H), 8.01–7.96 (m, 2H), 7.60 (dd, J = 7.0, 2.0 Hz, 1H), 7.48–7.46 (m, 1H), 7.38–7.31 (m, 2H), 6.46 (s, 1H) ppm; ¹³C NMR (100 MHz, DMSO-d₆): 157.1, 154.0, 151.6, 135.8, 135.2, 134.3, 131.7, 130.4, 130.2, 129.5, 129.2, 128.8, 128.3, 127.8, 127.2, 116.2, 61.1, 60.2 ppm; IR (KBr): υ = 3367, 3232, 3171, 2206, 1655, 1568, 1379 cm⁻¹.

4.2.5 3-Amino-1-(4-chlorophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile (4h)

Yellow powder; yield: 98%; mp = 272–274 °C; ¹H NMR (400 MHz, DMSO-d₆): δ_H 8.27-8.24 (m, 1H), 8.13 (brs, 2H, NH₂), 8.10–8.06 (m, 1H), 7.99–7.94 (m, 2H), 7.52 (d, J = 8.8 Hz, 2H), 7.43 (d, J = 8.8 Hz, 2H), 6.15 (s, 1H) ppm; ¹³C NMR (100 MHz, DMSO-d₆): 157.1, 154.1, 151.2, 151.1, 137.1, 135.1, 134.2, 133.3, 129.3, 129.4, 129.0, 128.1, 127.7, 127.1, 116.4, 62.7 ppm; IR (KBr): υ = 3371, 3257, 3114, 2196, 1656, 1566 cm⁻¹.

4.2.6 3-Amino-1-(4-Bromophenyl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile (4i)

Yellow powder; yield: 85%; mp = 267–268 °C; ¹H NMR (400 MHz, DMSO-d₆): δ_H 8.27-8.25 (m, 1H), 8.13 (brs, 2H, NH₂), 8.10-8.07 (m, 1H), 7.98–7.96 (m, 2H), 7.56 (d, J = 8.8 Hz, 2H), 7.46 (d, J = 8.8 Hz, 2H), 6.13 (s, 1H) ppm; ¹³C NMR (100 MHz, DMSO-d₆): 157.1, 154.1, 151.2, 138.4, 135.1, 134.2, 131.9, 129.6, 129.3, 129.0, 127.7, 127.1, 121.9, 116.4, 62.8, 61.3 ppm; IR (KBr): υ = 3371, 3257, 3193, 2194, 1655, 1560 cm⁻¹.

4.2.7 3-Amino-1-(pyridine carbaldehyde)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile (4j)

Yellow powder; yield: 86%; mp = 266–268 °C; ¹H NMR (400 MHz, DMSO-d₆): δ_H 8.73 (d, J= 1.6 Hz, 1H), 8.54 (dd, J = 4.8, 1.2 Hz, 1H), 8.27–8.25 (m, 1H), 8.17 (brs, 2H, NH₂), 8.10–8.08 (m, 1H), 7.99–7.96 (m, 2H), 7.94–7.92 (m, 1H), 7.40 (dd, J = 7.8, 4.4 Hz, 1H), 6.22 (s, 1H) ppm; IR (KBr): υ = 3364, 3259, 3193, 2189, 1652, 1569, 1383 cm⁻¹; Anal. calcd. for C₁₇H₁₁N₅O₂: C, 64.35; H, 3.49; N, 22.07. Found: C, 64.66; H, 3.27; N, 21.55.

4.2.8 3-Amino-1-(1-naphtalen-1-yl)-5,10-dioxo-5,10-dihydro-1H-pyrazolo[1,2-b] phthalazine-2-carbonitrile (4k)

Yellow powder; yield: 98%; mp = 276–278 °C; ¹H NMR (400 MHz, DMSO-d₆): δ_H 8.30–8.28 (m, 1H), 8.16 (brs, 2H, NH₂), 7.89–8.08 (m, 7H), 7.53–7.60 (m, 3H), 6.30 (s, 1H) ppm; ¹³C NMR (100 MHz, DMSO-d₆): 157.2, 154.2, 151.1, 151.0 136.3, 135.1, 134.2, 133.3, 133.1, 129.3, 129.1, 128.9, 128.3, 128.1, 127.8, 127.1, 126.9, 126.8, 126.5, 124.8, 116.6, 63.7 ppm; IR (KBr): υ = 3365, 3255, 3193, 2190, 1652, 1560 cm⁻¹; Anal. calcd. for C₂₂H₁₄N₄O₂: C, 72.12; H, 3.85; N, 15.29. Found: C, 72.71; H, 3.50; N, 15.52.

Acknowledgements

Financial support for this work by the research council of Islamic Azad University, Rasht Branch is gratefully acknowledged.

Bibliographie

[1] N.K. Terrett; A.S. Bell; D. Brown; P. Ellis Bioorg. Med. Chem. Lett., 6 (1996), p. 1819

[2] J. Elguero (A.R. Katritzky; C.W. Rees; E.F. Scriven, eds.), Comprehensive Heterocyclic Chemistry, vol. 3, Elsevier, 1996, p. 1

[3] S.K. Singh; P.G. Reddy; K.S. Rao; B.B. Lohray; P. Misra; S.A. Rajjak; Y.K. Rao; A. Venkatewarlu Bioorg. Med. Chem. Lett., 14 (2004), p. 499

[4] M.J. Genin; C. Biles; B.J. Keiser; S.M. Poppe; S.M. Swaney; W.G. Tarpley; Y. Yagi; D.L. Romero; D. O’Hagan J. Fluorine Chem., 43 (2000), p. 1034

[5] F. Al-Assar; K.N. Zelenin; E.E. Lesiovskaya; I.P. Bezhan; B.A. Chakchir Pharm. Chem. J., 36 (2002), p. 598

[6] R.P. Jain; J.C. Vederas Bioorg. Med. Chem. Lett., 14 (2004), p. 3655

[7] R.W. Carling; K.W. Moore; L.J. Street; D. Wild; C. Isted; P.D. Leeson; S. Thomas; D. O’Conner; R.M. McKernan; K. Quirk; S.M. Cook; J.R. Atack; K.A. Waftord; S.A. Thompson; G.R. Dawson; P. Ferris; J.L. Castro J. Med. Chem., 47 (2004), p. 1807

[8] S. Grasso; G. DeSarro; N. Micale; M. Zappala; G. Puia; M. Baraldi; C. Demicheli J. Med. Chem., 43 (2000), p. 2851

[9] Y. Nomoto; H. Obase; H. Takai; M. Teranishi; J. Nakamura; K.C. Kubo Chem. Pharm. Bull., 38 (1990), p. 2179

[10] N. Watanabe; Y. Kabasawa; Y. Takase; M. Matsukura; K. Miyazaki; H. Ishihara; K. Kodama; H. Adachi J. Med. Chem., 41 (1998), p. 3367

[11] M.R. Nabid; S.J.T. Rezaei; R. Ghahremanzadeh; A. Bazgir; R. Ghahremanzadeh; G.I. Shakibaei; A. Bazgir; D.S. Raghuvanshi; K.N. Singh; H.R. Shaterian; M. Mohammadnia; G. Karthikeyana; A. Pandurangan J. Mol. Catal. A: Chem., 17 (2010), p. 159

[12] M.N. Elinson; A.I. Ilovaisky; V.M. Merkulova; D.V. Demchuk; P.A. Belyakov; Y.N. Ogibin; G.I. Nikishin; M.N. Elinson; V.M. Merkulova; A.I. Ilovaisky; A.O. Chizhov; P.A. Belyakov; F. Barba; B. Batanero; M.N. Elinson; V.M. Merkulova; A.I. Ilovaisky; F. Barba; B. Batanero; M.N. Elinson; A.I. Ilovaisky; V.M. Merkulova; T.A. Zaminovskaya; G.I. Nikishin; M.N. Elinson; A.I. Ilovaisky; A.S. Dorofeev; V.M. Merkulova; N.O. Stepanov; F.M. Miloserdov; Y.N. Ogibin; G.I. Nikishin Tetrahedron, 53 (2008), p. 8346

Cité par

Benedikt W. Grau; Praveen Kumar; Aaron Nilsen; Sanjay V. Malhotra Nitrogen-bridgehead compounds: overview, synthesis, and outlook on applications, Organic Biomolecular Chemistry, Volume 23 (2025) no. 7, p. 1479 | DOI:10.1039/d4ob01589d
Zahra Karimi; Bahador Karami; Mahnaz Farahi; Aref Mahmoudi Asl Reinforced MOF/polymer composite based on a copper metal-organic framework supported on nanoporous hyper cross-linked polycalix[4]resorcinarene for the preparation of phthalazine and 4H-pyran heterocycles, Materials Today Chemistry, Volume 38 (2024), p. 102085 | DOI:10.1016/j.mtchem.2024.102085
Michail N. Elinson; Anatoly N. Vereshchagin; Yuliya E. Ryzhkova; Fedor V. Ryzhkov Electrochemical transformations of CH-acids, Mendeleev Communications, Volume 34 (2024) no. 2, p. 145 | DOI:10.1016/j.mencom.2024.02.001
Leila Moradi; Hamideh Rouhi Sasi; Abdulhamid Dehghani Introducing a high throughput nanocatalytic method toward the synthesis of some pyrazolo phthalazine derivatives under green conditions utilizing imidazoliume based ionic liquid supported on the silica-coated nanosized perlite as a novel, reusable and eco-friendly nanocatalyst, Research on Chemical Intermediates, Volume 50 (2024) no. 4, p. 1619 | DOI:10.1007/s11164-024-05234-4
S. G. Zlotin; K. S. Egorova; V. P. Ananikov; A. A. Akulov; M. V. Varaksin; O. N. Chupakhin; V. N. Charushin; K. P. Bryliakov; A. D. Averin; I. P. Beletskaya; E. L. Dolengovski; Yu. H. Budnikova; O. G. Sinyashin; Z. N. Gafurov; A. O. Kantyukov; D. G. Yakhvarov; A. V. Aksenov; M. N. Elinson; V. G. Nenajdenko; A. M. Chibiryaev; N. S. Nesterov; E. A. Kozlova; O. N. Martyanov; I. A. Balova; V. N. Sorokoumov; D. A. Guk; E. K. Beloglazkina; D. A. Lemenovskii; I. Yu. Chukicheva; L. L. Frolova; E. S. Izmest'ev; I. A. Dvornikova; A. V. Popov; A. V. Kutchin; D. M. Borisova; A. A. Kalinina; A. M. Muzafarov; I. V. Kuchurov; A. L. Maximov; A. V. Zolotukhina The green chemistry paradigm in modern organic synthesis, Russian Chemical Reviews, Volume 92 (2023) no. 12, p. RCR5104 | DOI:10.59761/rcr5104
Guglielmo A. Coppola; Serena Pillitteri; Erik V. Van der Eycken; Shu-Li You; Upendra K. Sharma Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency, Chemical Society Reviews, Volume 51 (2022) no. 6, p. 2313 | DOI:10.1039/d1cs00510c
Seyyed Jafar Kalantarian; Hassan Kefayati; Naser Montazeri Synthesis and antimicrobial evaluation of novel tris‐thiadiazole derivatives, Journal of Heterocyclic Chemistry, Volume 59 (2022) no. 7, p. 1253 | DOI:10.1002/jhet.4466
Ghodsi Mohammadi Ziarani; Negar Jamasbi; Fatemeh Mohajer Recent Achievements in the Synthesis of Heterocyclic Compounds by Phthalhydrazide-Based Multicomponent Reactions, HETEROCYCLES, Volume 102 (2021) no. 10, p. 1861 | DOI:10.3987/rev-20-953
Cinnathambi Subramani Maheswari; Rathinam Ramesh; Appaswami Lalitha Antibacterial Evaluation of Some 3-Amino-1H-Pyrazolo[1,2-b]Phthalazine-2-Carboxamides by using Fish Scale Hydroxyapatite as a Heterogeneous Catalyst, Polycyclic Aromatic Compounds, Volume 41 (2021) no. 10, p. 2221 | DOI:10.1080/10406638.2019.1711138
Mahdia Hamidinasab; Mohammad Ali Bodaghifard; Akbar Mobinikhaledi Green synthesis of 1H‐pyrazolo[1,2‐b]phthalazine‐2‐carbonitrile derivatives using a new bifunctional base–ionic liquid hybrid magnetic nanocatalyst, Applied Organometallic Chemistry, Volume 34 (2020) no. 2 | DOI:10.1002/aoc.5386
Cinnathambi Subramani Maheswari; Velmurugan Tamilselvi; Rathinam Ramesh; Appaswami Lalitha An Organocatalytic Cascade Synthesis of Diverse 1H-Pyrazolo[1,2-b]phthalazine-2-carboxamide,1H-Pyrazolo[1,2-b]phthalazine, 4H-Pyrano[2,3-c]pyrazole and 4H-Benzo[g]chromenes via Multicomponent Reactions, Organic Preparations and Procedures International, Volume 52 (2020) no. 1, p. 22 | DOI:10.1080/00304948.2019.1693241
Kadir TURHAN One-Pot Synthesis of Substituted Phthalazine-5,10-dione Derivatives in the Presence of Triflate Catalyst, Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, Volume 9 (2019) no. 1, p. 468 | DOI:10.21597/jist.433331
Omnyia Said Zaky; Maghraby Ali Selim; Manal Makboul Ebied; Kamal Usef Sadek Glycerol: A Promising Benign Solvent for Catalyst‐free One‐pot Multi‐component Synthesis of 1H‐Pyrozolo[1,2‐b]phthalazine‐5,10‐diones and 2H‐Indazolo[2,1‐b]phthalazine‐triones Under Controlled Microwaves Irradiation, Journal of Heterocyclic Chemistry, Volume 56 (2019) no. 10, p. 2796 | DOI:10.1002/jhet.3659
Somaye Nikzad Shalkouhi; Hassan Kefayati; Shahab Shariati Synthesis of novel spiro[chromeno[4′,3′:3,4]pyrazolo[1,2-b]phthalazine-7,3′-indoline]-2′,6,9,14-tetraone, Journal of the Iranian Chemical Society, Volume 16 (2019) no. 2, p. 263 | DOI:10.1007/s13738-018-1506-9
Sonatai Patil; Ananda Mane; Savita Dhongade-Desai CuO nanoparticles as a reusable catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions, Journal of the Iranian Chemical Society, Volume 16 (2019) no. 8, p. 1665 | DOI:10.1007/s13738-019-01640-3
Priya Arora; Jaspreet Kaur Rajput Amelioration of H4[W12SiO40] by nanomagnetic heterogenization: For the synthesis of 1H–pyrazolo[1,2‐b]phthalazinedione derivatives, Applied Organometallic Chemistry, Volume 32 (2018) no. 2 | DOI:10.1002/aoc.4001
Fereshteh Hatami Sabour; Mahboobeh Nasr-Esfahani; Iraj Mohammadpoor-Baltork; Shahram Tangestaninejad; Majid Moghadam; Valiollah Mirkhani A convenient approach for the synthesis of various derivatives of pyrazolo[1,2-b]phthalazinediones in the presence of an efficient supported basic ionic liquid at ambient temperature and solvent-free media, Journal of the Iranian Chemical Society, Volume 15 (2018) no. 3, p. 671 | DOI:10.1007/s13738-017-1267-x
Lida Fotouhi; Majid M. Heravi; Vahideh Zadsirjan; Paria Asadi Atoi Electrochemically Induced Michael Addition Reaction: An Overview, The Chemical Record, Volume 18 (2018) no. 11, p. 1633 | DOI:10.1002/tcr.201800022
Reza Tayebee; Behrooz Maleki; Mohammad sabeti A new simple method for the preparation of PbO nanoparticles and implementation of an efficient and reusable catalytic system for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones, Journal of the Iranian Chemical Society, Volume 14 (2017) no. 6, p. 1179 | DOI:10.1007/s13738-017-1068-2
Esma Lamera; Sofiane Bouacida; Hocine Merazig; Aissa Chibani; Marc Le Borgne; Zouhair Bouaziz; Abdelmalek Bouraiou DMAP as a new efficient catalyst for the one-pot synthesis of condensed phthalazines, Zeitschrift für Naturforschung B, Volume 72 (2017) no. 5, p. 361 | DOI:10.1515/znb-2016-0262
Michail N. Elinson; Anatoly N. Vereshchagin; Fedor V. Ryzhkov Catalysis of Cascade and Multicomponent Reactions of Carbonyl Compounds and CH Acids by Electricity, The Chemical Record, Volume 16 (2016) no. 4, p. 1950 | DOI:10.1002/tcr.201600044
Reyhaneh Kazemi‐Rad; Javad Azizian; Hassan Kefayati Improved Synthesis of 2,2‐Arylmethylene Bis(3‐hydroxy‐5,5‐dimethyl‐2‐cyclohexene‐1‐one) and 1,8‐Dioxo‐octahydroxanthene Derivatives Catalyzed by Electrogenerated Base and Sulfuric Acid, Journal of the Chinese Chemical Society, Volume 62 (2015) no. 4, p. 311 | DOI:10.1002/jccs.201400307
Ardeshir Khazaei; Mohammad Ali Zolfigol; Fatemeh Karimitabar; Iraj Nikokar; Ahmad Reza Moosavi-Zare N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media, RSC Advances, Volume 5 (2015) no. 87, p. 71402 | DOI:10.1039/c5ra10730j
Reyhaneh Kazemi-Rad; Javad Azizian; Hassan Kefayati Electrogenerated acetonitrile anions/tetrabutylammonium cations: an effective catalytic system for the synthesis of novel chromeno[3′,4′:5,6]pyrano[2,3-d]pyrimidines, Tetrahedron Letters, Volume 55 (2014) no. 50, p. 6887 | DOI:10.1016/j.tetlet.2014.10.099

Cité par 24 documents. Sources : Crossref

Commentaires - Politique