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Prins Spirocyclization for the Synthesis of Spiro[isobenzofuran‐pyran] Derivatives
Author(s) -
Reddy B. V. Subba,
Kumar Harish,
Reddy P. Sivaramakrishna,
Singarapu Kiran Kumar
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402157
Subject(s) - isobenzofuran , chemistry , pyran , prins reaction , hydroxymethyl , selectivity , bromide , stereochemistry , trifluoromethanesulfonate , cascade , organic chemistry , medicinal chemistry , chromatography , catalysis
A Prins cascade process was developed for the synthesis of tetrahydro‐3 H ‐spiro[isobenzofuran‐pyran] derivatives in good yields and selectivity by the condensation of 3‐[2‐(hydroxymethyl)phenyl]but‐3‐en‐1‐ols with aldehydes or ketones. The reaction proceeds smoothly in the presence of indium(III) trifluoromethanesulfonate (30 mol‐%) in dichloroethane at 80 °C. This is the first report on the synthesis of tetrahydro‐3 H ‐spiro[isobenzofuran‐pyran] scaffolds through a Prins cascade reaction.
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