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 |
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| Authors: | Anoop Singh Nisar A. Mir Sachin Choudhary Deepika Singh Preetika Sharma Rajni Kant Indresh Kumar |
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| Affiliation: | Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031 Rajasthan India.; Instrumentation Division, IIIM-CSIR Lab, Jammu 180 001 India ; X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu 180 006 India ; Department of Chemistry, Govt. Degree College for Pulwama-192301 J&K India |
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| Abstract: | An efficient sequential multi-component method for the synthesis of N-arylpyrrole-3-carbaldehydes has been developed. This reaction involved a proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and in situ 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.An efficient sequential multi-component method for the synthesis of N-arylpyrrole-3-carbaldehydes has been developed. |
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