3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization | Zendy

Manda Rajesh | Zendy; Maneesh Kumar Reddy Singam | Zendy; Ranjith Kumar Gadi | Zendy; Maddi Sridhar Reddy | Zendy

Open Access

3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization

Author(s) -

Manda Rajesh,

Maneesh Kumar Reddy Singam,

Ranjith Kumar Gadi,

Maddi Sridhar Reddy

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b02480

Subject(s) - propargyl , chemistry , bifunctional , catalysis , conjugate , nucleophile , reagent , organic chemistry , medicinal chemistry , combinatorial chemistry , mathematical analysis , mathematics

A facile route to 3-sulfonylated and 3-(1-benzotriazolyl)-benzofurans is achieved from readily available o -hydroxyphenyl propargyl alcohols ( o -HPPAs) and bench-top sodium sulfonylates and benzotriazoles with no assistance of any reagent or catalyst. Bifunctional o -quinone methides ( o -QMs) were the putative reaction intermediates ensued from dehydration of o -HPPA. Our study revealed that the o -QM was so choosy in selection of the nucleophiles for the key Michael addition reaction.

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