Facile Domino Access to Unexpected Alkyl 3-Substituted-2-hydroxy-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates
Ya-Ru Zhang A , Xiao Huang A , Dong-Cheng Xu A and Jian-Wu Xie A B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry and Life Science, Zhejiang Normal University, 321004 Jinhua, China.
B Corresponding author. Email: xiejw@zjnu.cn
Australian Journal of Chemistry 66(8) 959-962 https://doi.org/10.1071/CH13103
Submitted: 1 March 2013 Accepted: 30 April 2013 Published: 29 May 2013
Abstract
A new domino alkylation–cyclization–air-oxidation of 2-halo-1,3-dicarbonyl compounds with 2-aminophenols promoted by caesium salts under aerobic conditions has been developed. Unexpected alkyl 3-substituted-2-hydroxy-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylates, rather than normal ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate, were exclusively obtained under mild conditions. A plausible mechanism for this unprecedented reaction is also given.
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