One-Pot Unsymmetrical {[4 + 2] and [4 + 2]} Double Annulations of o/o′-C–H Bonds of Arenes: Access to Unusual Pyranoisoquinolines

Shankar, Majji ; Ghosh, Koushik ; Mukherjee, Kallol ; Rit, Raja K. ; Sahoo, Akhila K. (2018) One-Pot Unsymmetrical {[4 + 2] and [4 + 2]} Double Annulations of o/o′-C–H Bonds of Arenes: Access to Unusual Pyranoisoquinolines Organic Letters, 20 (17). pp. 5144-5148. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.8b02068

Related URL: http://dx.doi.org/10.1021/acs.orglett.8b02068

Abstract

With the aid of a transformable sulfoximine directing group, unprecedented one-pot unsymmetrical double annulations {[4 + 2] and [4 + 2]} of hetero(arenes) with alkynes are revealed under Ru(II) catalysis. Functionalization of both ortho-C–H bonds of (hetero)arene is reflected in the building of unusual 6,6-fused pyranoisoquinoline skeletons. Construction of four [(C–C)–(C–N) and (C–C)–(C–O)] bonds occurs in one step under single catalytic conditions. The challenging unsymmetrical double annulations of both o-C–H bonds of arenes with two distinct alkynes is effectively demonstrated. Control experiments and deuterium scrambling findings are shown.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:121867
Deposited On:22 Jul 2021 18:27
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