Synthesis of 6-amino-4-aryl-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles by heterogeneous reusable catalysts

被引：20

作者：

Shaterian, Hamid Reza ^{[1
]}

Kangani, Mehrnoosh ^{[1
]}

机构：

[1] Univ Sistan & Baluchestan, Dept Chem, Fac Sci, Zahedan, Iran

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2014年 / 40卷 / 05期

关键词：

Four-component reaction; Solvent-free; 1,4-Dihydropyrano[2,3-c]pyrazoles; Ethyl acetoacetate; Arylaldehydes; Malononitrile; ONE-POT SYNTHESIS; MULTICOMPONENT SYNTHESIS; SULFURIC-ACID; PYRANOPYRAZOLES; EFFICIENT; CELLULOSE; ALUMINA;

D O I：

10.1007/s11164-013-1097-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new, efficient and environmentally benign protocol for the one-pot, four-component synthesis of 1,4-dihydropyrano[2,3-c]pyrazoles by reaction of hydrazine monohydrate, ethyl acetoacetate, arylaldehydes and malononitrile in the presence of a green catalytic amount of P2O5/SiO2, H3PO4/Al2O3, cellulose sulfuric acid and starch sulfuric acid is described. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages of this method.

引用

页码：1997 / 2005

页数：9

共 50 条

[31] A new and straightforward route to synthesize novel pyrazolo[3,4-b]pyridine-5-carboxylate scaffolds from 1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles
Nguyen, Hai Truong
Dang, Phu Hoang
Tran, Phuong Hoang
RSC ADVANCES, 2023, 13 (03) : 1877 - 1882
[32] Synthesis and antimicrobial activity of new 6-amino-4-phenyl-1-(N-alkoxyphthalimido)-3-methyl-1,4-dihydro pyrano[2,3-c]pyrazole-5-carbonitriles
Jat, Jawahar L.
Bhambi, Dinesh
Chaudhary, Jyoti
Talesara, G. L.
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 16 (02) : 113 - 116
[33] A green and one-pot synthesis of 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile derivatives using CoCeO2 nanoparticles as an efficient, reusable and heterogeneous catalyst
Shaheen A. Shaikh
Vishal S. Kamble
Rohan K. Zemase
Sanjay K. Patil
Balasaheb D. Aghav
Research on Chemical Intermediates, 2023, 49 : 5255 - 5272
[34] Synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using nano-ZnZr4(PO4)(6) as an efficient catalyst
Safaei-Ghomi, Javad
Asgari-Kheirabadi, Mehrnoosh
Shahbazi-Alavi, Hossein
Ziarati, Abolfazl
IRANIAN JOURNAL OF CATALYSIS, 2016, 6 (04): : 319 - 324
[35] A Practical Catalyst-Free Synthesis of 6-Amino-4 Alkyl/Aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-carbonitrile in Aqueous Medium
Bihani, Manisha
Bora, Pranjal P.
Bez, Ghanashyam
JOURNAL OF CHEMISTRY, 2013, 2013
[36] A facile synthesis of 6-amino-2H, 4H-pyrano[2,3-c]pyrazole-5-carbonitriles in deep eutectic solvent
Bhosle, Manisha R.
Khillare, Lalit D.
Dhumal, Sambhaji T.
Mane, Ramrao A.
CHINESE CHEMICAL LETTERS, 2016, 27 (03) : 370 - 374
[37] Synthesis and potential biological activity of some novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles
Mandour, Adel Hamed
El-Sawy, Eslam Reda
Ebaid, Manal Shaaban
Hassan, Seham M.
ACTA PHARMACEUTICA, 2012, 62 (01) : 15 - 30
[38] Green Approach to the Design of Functionalized Medicinally Privileged 4-Aryl-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile Scaffold
Ilovaisky, Alexey I.
Medvedev, Michael G.
Merkulova, Valentina M.
Elinson, Michail N.
Nikishin, Gennady I.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (02) : 523 - 526
[39] Green synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives using maltose as biodegradable catalyst
Mehrnoosh Kangani
Nourallah Hazeri
Malek Taher Mghsoodlou
Sayyed Mostafa Habibi-khorasani
Sajjad Salahi
Research on Chemical Intermediates, 2015, 41 : 2513 - 2519
[40] 6-Amino-1-benzyl-4-(4-chlorophenyl)-3-(4-pyridyl)-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitrile
Lehmann, Frank
Schollmeyer, Dieter
Laufer, Stefan
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O701 - U1277

← 1 2 3 4 5 →