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BF 3 ·OEt 2 ‐Mediated Synthesis of 2‐Arylthio‐ and ( N ‐Aryl‐2,5‐dioxopyrrolidin‐3‐yl)‐Substituted 1,4‐Benzoxazine Derivatives
Author(s) -
Sharma Shivangi,
Kumar Pravin,
Sharma Arun,
Peddinti Rama Krishna
Publication year - 2017
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.201700407
Subject(s) - chemistry , diastereomer , adduct , aryl , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , alkyl
1,4‐Benzoxazines have been explored as versatile precursors for the synthesis of novel benzoxazine and benzoxazinone derivatives. 2‐Hydroxy‐1,4‐benzoxazines and 1,4‐benzoxazinones have been functionalized with thiols and N ‐arylmaleimides, respectively, in the presence of BF 3 · OEt 2 as a promoter. All the products were obtained in moderate to excellent yields. The Michael reactions of the benzoxazinones with maleimides furnished diastereomeric mixtures of adducts, which were characterized by standard spectroscopic methods.