SYNTHESIS OF 6-AMINO-2,4-DIHYDROPYRANO[2,3-c]PYRAZOL-5-CARBONITRILES CATALYZED BY SILICA-SUPPORTED TETRAMETHYLGUANIDINE UNDER SOLVENT-FREE CONDITIONS

被引：42

作者：

Atar, Amol B. ^{[1
]}

Kim, Jong Tae ^{[1
]}

Lim, Kwon Taek ^{[1
]}

Jeong, Yeon Tae ^{[1
]}

机构：

[1] Pukyong Natl Univ, Dept Image Sci & Engn, Pusan 608737, South Korea

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 18期

关键词：

Four-component reaction; heterogeneous catalyst; pyrano[2; 3-c]pyrazole; silica-supported tetramethylguanidine; ONE-POT SYNTHESIS; MULTICOMPONENT SYNTHESIS; HIGHLY EFFICIENT; RAPID SYNTHESIS; PYRANOPYRAZOLES; 4-COMPONENT; DERIVATIVES; CONDENSATION; GEL;

D O I：

10.1080/00397911.2014.913634

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, high-yielding, and rapid protocol has been developed for the synthesis of diversity-oriented 6-amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles derivatives via a four-component, one-pot cyclocondensation reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile using silica-supported tetramethylguanidine as a heterogeneous catalyst for the first time. The protocol proves to be efficient and environmentally benign in terms of very easy workup, good yields, and ease of recovery of catalyst. In addition, the present method is superior in terms of green media, the amount of catalyst, and reaction time.

引用

页码：2679 / 2691

页数：13

共 50 条

[31] Screening, synthesis, crystal structure, and molecular basis of 6-amino-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles as novel AKR1C3 inhibitors
Zheng, Xuehua
Jiang, Zan
Li, Xiaolin
Zhang, Chen
Li, Zhe
Wu, Yinuo
Wang, Xinhua
Zhang, Chao
Luo, Hai-bin
Xu, Jun
Wu, Deyan
BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (22) : 5934 - 5943
[32] [DBU][Ac]-catalyzed mild preparation of 6-amino-4-aryl-5-cyano-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole derivatives
Hamid Reza Shaterian
Marziyeh Sedghipour
Ebrahim Mollashahi
Research on Chemical Intermediates, 2014, 40 : 2721 - 2728
[33] [DBU][Ac]-catalyzed mild preparation of 6-amino-4-aryl-5-cyano-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole derivatives
Shaterian, Hamid Reza
Sedghipour, Marziyeh
Mollashahi, Ebrahim
RESEARCH ON CHEMICAL INTERMEDIATES, 2014, 40 (08) : 2721 - 2728
[34] Nano-SiO2/hexamethylenetetramine promoted synthesis of pyrano[2,3-c] pyrazoles under solvent-free conditions
Mirjalili, Bi Bi Fatemeh
Keihanfar, Mina
IRANIAN JOURNAL OF CATALYSIS, 2020, 10 (01): : 17 - 22
[35] A clean and simple synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole in water
Jin, TS
Wang, AQ
Cheng, ZL
Zhang, JS
Li, TS
SYNTHETIC COMMUNICATIONS, 2005, 35 (01) : 137 - 143
[36] EFFICIENT AND FACILE SYNTHESIS OF 2,4-DIAMINO-6-ARYLPYRIMIDINE-5-CARBONITRILE UNDER SOLVENT-FREE CONDITIONS
Rong, Liangce
Han, Hongxia
Gao, Lijiu
Dai, Yisi
Cao, Minxia
Tu, Shujiang
SYNTHETIC COMMUNICATIONS, 2010, 40 (04) : 504 - 509
[37] Silica-supported synthesis of some 1,3,5-trisubstituted 2-pyrazolines under solvent-free and microwave irradiation conditions
Azarifar, D
Maleki, B
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (01) : 157 - 159
[38] Synthesis of 3-methyl-6-amino-5-cyano-4-aryl-1-phenyl-1,4-dihydropyrano [2,3-c]pyrazole catalysed by KF-montmorillonite
Wu, Nan
Li, Xinnian
Wang, Yumei
Shi, Daqing
JOURNAL OF CHEMICAL RESEARCH, 2008, (01) : 16 - 17
[39] PIPERAZINE CATALYZED ONE-POT, THREE-COMPONENT SYNTHESIS OF 4H-CHROMENE AND 3,4-DIHYDROPYRANO[c]CHROMENE DERIVATIVES UNDER SOLVENT-FREE CONDITIONS
Mobinikhaledi, Akbar
Moghanian, Hassan
Zohari, Azam
REVUE ROUMAINE DE CHIMIE, 2016, 61 (01) : 35 - +
[40] Visible light promoted synthesis of dihydropyrano-[2,3-c]chromenes via a multicomponent-tandem strategy under solvent and catalyst free conditions
Tiwari, Jyoti
Saquib, Mohammad
Singh, Swastika
Tufail, Fatima
Singh, Mandavi
Singh, Jaya
Singh, Jagdamba
GREEN CHEMISTRY, 2016, 18 (11) : 3221 - 3231

← 1 2 3 4 5 →