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Oxa-[3+3] annulation of MBH-carbonates of propiolaldehydes with α-nitro/bromo ketones to access 2H-pyrans

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Abstract

A novel alkyne-assisted annulation reaction of MBH-carbonates of propiolaldehydes with α-nitro/bromo ketones is reported, providing a facile synthesis of substituted 2H-pyrans in good yields. This reaction divulges the inimitable reactivity of the MBH-carbonates of propiolaldehydes as C3-synthons wherein the alkyne functionality promoted the reaction without participating in the oxa-[3+3] annulation. The obtained products, having alkyne and ester functionalities, allowed further annulations to generate diverse pyrano[3,4-c]pyran-1-ones.

Graphical abstract: Oxa-[3+3] annulation of MBH-carbonates of propiolaldehydes with α-nitro/bromo ketones to access 2H-pyrans

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Article information


Submitted
23 Apr 2020
Accepted
18 May 2020
First published
19 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Oxa-[3+3] annulation of MBH-carbonates of propiolaldehydes with α-nitro/bromo ketones to access 2H-pyrans

C. R. Reddy, A. D. Patil and S. Z. Mohammed, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02947E

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