Cyclic Guanidines. I. Synthesis of Hypoglycemic 1-Substituted 2-Imino-1,3-diazacycloalkanes
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概要
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Reaction of 2-benzylaminoethylamine (1a) with cyanogen bromide was investigated under various conditions to obtain desired 1-benzyl-2-iminoimidazolidine (2a) in quantitative yield. In addition, in the presence of base this reaction gave 3-carbamoyl derivative (3a) or 3-methoxyformimidoyl derivative (6) of 2a. The 3-carbamoyl group of 3a was rearranged to the 2-imino group on heating to give 2-carbamoylimino derivative (5a). On the other hand, 6 was derived to 3a or 3-methoxycarbonyl derivative (7) by heating under strong or mild acidic medium, respectively. 3-Amidino-1-benzyl-2-iminoimidazolidine (9) was prepared through 2-benzylaminoethylguanidine (8) from 1a. 1-Benzyl- or 1-benzhydryl-2-cyanoimino-1,3-diazacycloalkanes (10) having five-, six- and seven-membered ring size were obtained on heating of 1 with dimethyl cyanoimidodithiocarbonate and then the cyano group of 10 was selectively removed to yield 1-benzyl- or 1-benzhydryl-2-imino-1,3-diazacycloalkanes (2). Some of 1-substituted 2-imino-1,3-diazacycloalkane derivatives showed hypoglycemic activity.
- 公益社団法人日本薬学会の論文
- 1978-12-25
著者
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今野 常生
Research Institute Daiichi Seiyaku Co. Ltd.
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小笹山 瑛
Research Institute, Daiichi Seiyaku Co., Ltd.
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石川 文義
Research Institute, Daiichi Seiyaku Co., Ltd.
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石川 文義
Research Institute Daiichi Seiyaku Co. Ltd.
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小笹山 瑛
第一製薬
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中村 薫竹
Research Institute, Daiichi Seiyaku Co., Ltd.
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小笹山 瑛
Research Institute Daiichi Seiyaku Co. Ltd.
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中村 薫竹
Research Institute Daiichi Seiyaku Co. Ltd.
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