One-pot sequential multicomponent reaction between in situ generated aldimines and succinaldehyde: facile synthesis of substituted pyrrole-3-carbaldehydes and applications towards medicinally important fused heterocycles

An efficient sequential multi-component method for the synthesis of -arylpyrrole-3-carbaldehydes has been developed. This reaction involved a proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and generated Ar/HetAr/indolyl-imines, followed by IBX-mediated oxidativ...

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Bibliographic Details
Published in:RSC advances 2018-01, Vol.8 (28), p.15448-15458
Main Authors: Singh, Anoop, Mir, Nisar A, Choudhary, Sachin, Singh, Deepika, Sharma, Preetika, Kant, Rajni, Kumar, Indresh
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Imines
Proline
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Summary:An efficient sequential multi-component method for the synthesis of -arylpyrrole-3-carbaldehydes has been developed. This reaction involved a proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and generated Ar/HetAr/indolyl-imines, followed by IBX-mediated oxidative aromatization in one-pot operation. The practical utility of this procedure is shown at gram-scale and the synthesis of diverse bioactive fused heterocyclic scaffolds such as pyrroloquinoline, pyrrolo-oxadiazole, dihydro pyrroloquinoline, and pyrrolo-phenanthridine.
ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra01637b