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A Concise Approach for the Synthesis of the ABCD Ring System of Alpkinidine
Author(s) -
Volvoikar Prajesh S.,
Tilve Santosh G.,
Zubkov Fedor I.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900357
Subject(s) - annulation , negishi coupling , ring (chemistry) , chemistry , stereochemistry , base (topology) , combinatorial chemistry , mathematics , organic chemistry , catalysis , mathematical analysis
A two step synthesis of a benzo analog of alpkinidine is described via Negishi coupling followed by a base mediated annulation reaction strategy. The organozinc compound prepared from ethyl 2‐iodobenzoate was coupled with 4‐chloro‐2‐methyl‐2,3‐dihydro‐1 H ‐pyrrolo[3,4‐ c ]quinolin‐1‐one to obtain ethyl 2‐(2‐methyl‐1‐oxo‐2,3‐dihydro‐1 H ‐pyrrolo[3,4‐ c ]quinolin‐4‐yl)‐benzoate which on further treatment with a base provided ABCD ring system of alpkinidine.