Type: Article

A four-component reaction: regio- and chemoselective formation of 7-amino-2-(tert-butyl)-5-aryl-4,5-dihydropyrazolo[1,5-a]pyrimidine-6-carbonitrile

Journal: Molecular Diversity (13811991)Year: 2020/08/01Volume: 24Issue: 3Pages: 753 - 761

Alizadeh-Kouzehrash M.Rahmati A.^a

a :University of Isfahan - IRAN(IR) - Isfahan

DOI:10.1007/s11030-019-09976-xLanguage: English

Abstract

Abstract: A novel one-pot four-component reaction of an aldehyde, malononitrile, hydrazine and 4,4-dimethyl-3-oxopentanenitrile is described. As regio- and chemoselective products, 7-amino-2-(tert-butyl)-5-aryl-4,5-dihydropyrazolo[1,5-a]pyrimidine-6-carbonitriles are formed during the course of the reaction. Graphic abstract: [Figure not available: see fulltext.]. © 2019, Springer Nature Switzerland AG.

Author Keywords

Multi-component reactionsPyrazolopyridinePyrazolopyrimidineStructure effect

Other Keywords

Chemistry Techniques, SyntheticKineticsNitrilesPyrazolesStereoisomerism5 [(1,1' dbiphenyl) 4 yl] 7 amino 2 (tert butyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 (3,4 dimethoxyphenyl)pyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 (4 bromophenyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 (4 cyanophenyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 (4 fluorophenyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 (4 isopropylphenyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 (4 methoxyphenyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 (4 nitrophenyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 (4 tolyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 2 (tert butyl) 5 aryl 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile derivative7 amino 2 (tert butyl) 5 [4 (naphthalen 2 yl)phenyl] 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 5 (4 chlorophenyl) 4,5 dihydropyrazolo[1,5 a]pyrimidine 6 carbonitrile7 amino 5 (benzo[d][1,3]dioxol 5 yl) 2 (tert butyl)pyrazolo[1,5 a]pyrimidine 6 carbonitrilealdehydehydrazinemalononitrilepyrazolopyrimidine derivativeunclassified drugnitrilepyrazole derivativeArticlecontrolled studydrug structuredrug synthesisone pot synthesispriority journalregioselectivitychemistrysynthesis