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Paper | Regular issue | Vol 57, No. 3, 2002, pp.429-437
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9396
Silver Ion-mediated Desulfurization of N,N-Disubstituted 2-Hydroxythiobenzamides

Isao Shibuya,* Kazumasa Honda, Yasuo Gama, and Masao Shimizu

*National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan


Silver ion–mediated desulfurization of N-(2- hydroxythiobenzoyl)morpholine (1a) or -piperidine (1b) was used to develop a new synthetic method for heterocycles such as 1,3-benzoxazin-1-ium salts. 2-Amino-4-morpholino- and 2-amino-4-piperidino-1,3-benzoxazin-1-ium perchlorate (2a, 2b) or 2-(N,N-dimethylamino)-4-morpholino- and 2-(N,N- dimethylamino)-4-piperidino-1,3-benzoxazin-1-ium perchlorate (3a, 3b) were obtained by treatment of 1a and 1b, respectively,with silver perchlorate in the presence of excess cyanamide or N,N-dimethylcyanamide, and the structure of 3a was confirmed by X-Ray crystallography. Desulfurization of 1 with AgOCN afforded 1,3-benzoxazin-2-ones (4). In addition, treatment of 1 with methyl cyanoacetate in the presence of silver trifluoroacetate and triethylamine gave 3-cyanochromen-2-ones (5).