Cyclofunctionalization of Olefinic Urethanes and Ureas with Halogens. : Synthesis of 1-Substituted Spiro[piperidine-4,4'(3'H)-quinazolin]-2'(1'H)-one Derivatives

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概要

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• The cyclization reaction of 4-(2-carbamoylaminophenyl)-1,2,5,6,-tetrahydropyridine derivatives (9) and a 4-(2-methoxycarbonylaminophenyl)-1,2,5,6,-tetrahydropyridine derivative (4) with halogen was investigated. Treatment of the former (9) with bromine or N-chlorosuccinmide (NCS) under acidic conditions gave the corresponding 3'-halogeno-2-amino-spiro[4H-3,1-benzoxazine-4,4'-piperidine] derivatives (11) and with iodine under basic conditions gave 5,6-dihydro-3-iodo-spiro[pyridine-4(1H), 4'-(3'H)-quinazolin]-2'(1'H)-one derivatives (14), which were converted to spiro[piperidine-4,4'(3'H)-quinazolin]-2'(1'H)-one derivatives (15 and 17). Treatment of the latter (4) with bromine under acidic conditions gave 3'-bromo-spiro[4H-3,1-benzoxazine-4,4'-piperidin]-2(1H)-one derivatives (5 and 6).

• 公益社団法人日本薬学会の論文
• 1988-12-25

著者

• 小場瀬 宏之

  Tokyo Research Laboratory, Kyowa Hakko Kogyo Co., Ltd.

• 寺西 正行

  Tokyo Research Laboratories Kyowa Hakko Kogyo Co. Ltd.

• 高井 春樹

  Tokyo Research Laboratory, Kyowa Hakko Kogyo Co., Ltd.,

• 高井 春樹

  Pharmaceutical Research Laboratories, Fuji, Kyowa Hakko Kogyo Co., Ltd.,

• 小場瀬 宏之

  Pharmaceutical Research Laboratories Kyowa Hakko Kogyo Co. Ltd.

• 高井 春樹

  Pharmaceutical Research Laboratories Fuji Kyowa Hakko Kogyo Co. Ltd.

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