Download PDF
Synfacts 2008(8): 0800-0800  
DOI: 10.1055/s-2008-1077942
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Benzoxazinones via Smiles Rearrangement

Contributor(s): Victor Snieckus, Jignesh J. Patel
H. Zuo, L. Meng, M. Ghate, K.-H. Hwang, Y. K. Cho, S. Chandrasekhar, Ch. R. Reddy, D.-S. Shin*
Changwon National University, South Korea; Indian Institute of Chemical Technology, Hyderabad, India; Southwest University, Chongqing, P. R. of China
Further Information

Publication History

Publication Date:
23 July 2008 (online)

    Permissions and Reprints

Significance

Reported here is a microwave assisted, one-pot, three-component route to benzo[b][1,4]oxazin-3(4H)-ones via Smiles rearrangement. Based on the previous work by the authors, Cs2CO3 was found to be the base of choice for the reaction of 2-chlorophenols with chloroacetyl chloride and primary amines under microwave irradiation at 150 ˚C to give substituted ben­-zo-[b][1,4]oxazin-3(4H)-ones in good to excellent yield. The Smiles rearrangement (mechanism shown) is usually favored by EWGs (W. E. Truce, E. M. Kreider, W. W. Brand Org. React. 1970, 18, 99); the scope of substituent effects was not well tested.