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

A novel alkyne-assisted annulation reaction of MBH-carbonates of propiolaldehydes with α-nitro/bromo ketones is reported, providing a facile synthesis of substituted 2 H -pyrans in good yields. This reaction divulges the inimitable reactivity of the MBH-carbonates of propiolaldehydes as C3-synthons...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-07, Vol.56 (52), p.7191-7194
Main Authors: Reddy, Chada Raji, Patil, Amol D., Mohammed, Siddique Z.
Format: Article
Language:English
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Summary:A novel alkyne-assisted annulation reaction of MBH-carbonates of propiolaldehydes with α-nitro/bromo ketones is reported, providing a facile synthesis of substituted 2 H -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.
ISSN:1359-7345
1364-548X
DOI:10.1039/D0CC02947E