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Synthesis of Functionalized Arenopyrans and Arenylsulfanes by Reacting Nitroallylic Acetates with Arenols and Arenethiols
Author(s) -
Basu Pallabita,
Sikdar Robi,
Kumar Tarun,
Namboothiri Irishi N. N.
Publication year - 2018
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.201801132
Subject(s) - chemistry , annulation , stereoselectivity , intramolecular force , phenols , medicinal chemistry , reaction conditions , organic chemistry , stereochemistry , catalysis
Nitroallylic acetates react with naphthols and electron‐rich phenols under mild conditions (TEA, DCM, room temp.) to afford arenopyrans in moderate to excellent yields. Such (3+3) annulation of a 1,3‐bielectrophilic nitroallylic acetate and a 1,3‐binucleophilic arenol involving an S N 2′ reaction and an intramolecular 6‐ endo ‐trig cyclization takes place in a regio‐ and stereoselective manner. Surprisingly, the reaction of arenethiols under the same conditions provided nitroallylic thioethers instead of the expected arenothiopyrans presumably through a direct S N 2 reaction.