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One‐Pot Synthesis of 1,4‐Dihydro‐2‐thioxo‐2 H ‐3,1‐benzoxazine‐4‐acetic Acid Derivatives by the Reaction of 2‐Isothiocyanatophenyl Ketones with Lithium Enolates of Acetates and Tertiary Acetamides
Author(s) -
Kobayashi Kazuhiro,
Fukamachi Shuhei,
Kobayashi Akihiro,
Gotoh Aogu
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200096
Subject(s) - chemistry , acetic acid , lithium (medication) , aryl , medicinal chemistry , organic chemistry , medicine , alkyl , endocrinology
Abstract The one‐pot synthesis of 4‐aryl‐1,4‐dihydro‐2‐thioxo‐2 H ‐3,1‐benzoxazine‐4‐acetic acid derivatives 2 was achieved in good yields by the reaction of aryl(2‐isothiocyanatophenyl)methanones 1 with lithium enolates of acetates and tertiary acetamides. (2 E )‐1‐(2‐Isothiocyanatophenyl)‐3‐phenylprop‐2‐en‐1‐one ( 3 ) gave 1,4‐dihydro‐4‐[(1 E )‐2‐phenylethenyl]‐2‐thioxo‐2 H ‐3,1‐benzoxazine‐4‐acetic acid derivatives 4 in good yields as well.