Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach

5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke-Blackburn-Bienaymé reaction (GBB reaction). Besides the syntheti...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2014-10, Vol.10 (1), p.2338-2344
Main Authors: Demjén, András, Gyuris, Márió, Wölfling, János, Puskás, László G, Kanizsai, Iván
Format: Article
Language:English
Subjects:
1H-imidazo[1,2-b]pyrazole
Chemistry
Full Research Paper
Groebke–Blackburn–Bienaymé reaction
isocyanide
multicomponent reaction
N-heterocycles
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Summary:5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke-Blackburn-Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe an operationally simple, one-pot two-step GBB protocol for the rapid construction of a 46 membered imidazo[1,2-b]pyrazole library with yields up to 83%.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.10.243