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Iodine-Promoted N–H/α,β-C(sp³)-Trifunctionalization of l-Proline: Access to 3,4-Dihydrobenzo[b][1,7]naphthyridines via Consecutive Decarboxylation/Ring Opening/Dicyclization

Author:
Geng, Xiao, Wang, Can, Zhao, Peng, Zhou, You, Wu, Yan-Dong, Wu, An-Xin
Source:
Organic letters 2019 v.21 no.13 pp. 4939-4943
ISSN:
1523-7052
Subject:
chemical structure, decarboxylation, heterocyclic nitrogen compounds, metabolism, proline, reaction mechanisms
Abstract:
A N–H/α,β-C(sp³)-trifunctionalization of l-proline, proceeding through an iodine-promoted consecutive decarboxylation/ring-opening/dicyclization process, is achieved. This strategy affords structurally diverse fused N-heterocycles in good yields with a wide substrate scope. Preliminary mechanistic studies indicate that catabolism of l-proline might be involved in this cascade reaction and the in situ generated intermediate 4-aminobutanal was identified as the key intermediate. Notably, this domino strategy enriches the reactivity of versatile l-proline in the synthesis of fused heterocycles.
Agid:
6496872