A Concise Approach for the Synthesis of the ABCD Ring System of Alpkinidine

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‐1H‐pyrrolo[3,4‐c]quinolin‐1‐one to obtain ethyl...

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Bibliographic Details
Published in:	ChemistrySelect (Weinheim) Vol. 4; no. 24; pp. 7187 - 7189
Main Authors:	Volvoikar, Prajesh S., Tilve, Santosh G., Zubkov, Fedor I.
Format:	Journal Article
Language:	English
Published:	28-06-2019
Subjects:	Alpkinidine Heterocycles Marine alkaloid Negishi Pyrroloacridine
Online Access:	Get full text
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Summary:	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‐1H‐pyrrolo[3,4‐c]quinolin‐1‐one to obtain ethyl 2‐(2‐methyl‐1‐oxo‐2,3‐dihydro‐1H‐pyrrolo[3,4‐c]quinolin‐4‐yl)‐benzoate which on further treatment with a base provided ABCD ring system of alpkinidine. A simple and efficient approach is established for the construction of the ABCD ring system of alpikinidine using Negishi coupling followed by anion mediated annulation of isoindolinone.
Bibliography:	birthday th Dedicated to Prof. B. R. Srinivasan on the occasion of his 60
ISSN:	2365-6549 2365-6549
DOI:	10.1002/slct.201900357