Calcium-Catalyzed Stereoselective Tandem [4+2] and [3+2] Annulation Reaction for the Synthesis of Dihydropyrrolo[1,2- A[quinolines

Ravikrishna Dada, Mahesh Sulthan, Srinivasarao Yaragorla

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17 Scopus citations

Abstract

Calcium-catalyzed highly facile one-pot, A4 annulation of aldehyde, amine, alkene, and alkyne to form fused 4,5-dihydropyrrolo[1,2-a]quinolines with exclusive syn diastereoselectivity is reported. This selectivity arises from an inverse electron demand [4+2] aza-Diels-Alder cycloaddition, and the adduct further undergoes a formal [3+2] cyclization with activated alkynes. This diversity-oriented protocol is highly general and furnishes the dihydropyrrolo[1,2-a]quinoline derivatives with a broad substrate scope in good to excellent yields.

Original languageEnglish (US)
Pages (from-to)279-283
Number of pages5
JournalOrganic Letters
Volume22
Issue number1
DOIs
StatePublished - Jan 3 2020
Externally publishedYes

Bibliographical note

Funding Information:
S.Y. gratefully acknowledges the financial support by SERB-2016/4812 and UGC-CAS. R.D. thanks SERB for the fellowship. M.S. thanks the School of Chemistry, UGC-NRC, for the facilities.

Publisher Copyright:
Copyright © 2019 American Chemical Society.

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