A palladium-catalyzed facile and general method for the stereoselective synthesis of (E)-3-arylidene-3,4-dihydro-2H-1,4-benzoxazines and their naphthoxazine analogues

作者：Brahma Kaushik; Das Bimolendu; Chowdhury Chinmay^*

来源：Tetrahedron, 2014, 70(35): 5863-5871.

DOI：10.1016/j.tet.2014.06.036

• 1,4-Benzoxazine
• 1,4-Naphthoxazine
• Palladium catalyst
• Stereoselective
• Cyclization

Palladium-catalyzed cyclocondensation of an aryl iodide with N-tosyl-2-(prop-2'-ynyloxy)aniline at room temperature is shown to constitute a convenient general method for the synthesis of (E)-3-arylidene-3,4-dihydro-2H-1,4-benzoxazines in moderate to very good yields. The method could also be extended to the synthesis of (E)-3-arylidene-2H-naphth[1,2-b][1,4]oxazines. The regio- and stereo-selectivity of the process, short reaction time, operational simplicity, and use of inexpensive starting materials represent its attractive features.

• 出版日期2014-9-2