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

ABSTRACT: 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%.

SUBMITTER: Demjen A 

PROVIDER: S-EPMC4222397 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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

Demjén András A   Gyuris Márió M   Wölfling János J   Puskás László G LG   Kanizsai Iván I  

Beilstein journal of organic chemistry 20141008

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 imid  ...[more]

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