Fused pyrimidine systems: XV. Intramolecular electrophilic cyclization of 2-allyl(propargyl, cinnamyl)amino-pyrido[2,3-d]pyrimidin-4(3H)-ones

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• 作者：R. I. Vas鈥檏evich ; I. V. Dyachenko ; A. I. Vas鈥檏evich…
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2015
• 出版时间：April 2015
• 年：2015
• 卷：51
• 期：4
• 页码：556-565
• 全文大小：292 KB
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• 作者单位：R. I. Vas鈥檏evich (1)
  I. V. Dyachenko (1)
  A. I. Vas鈥檏evich (2)
  E. B. Rusanov (1)
  M. V. Vovk (1)
  
  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02660, Ukraine
  2. 鈥淜yiv Polytechnic Institute鈥?National Technical University of Ukraine, pr. Peremohy 37, Kiev, 03056, Ukraine
  
• 刊物主题：Organic Chemistry;
• 出版者：Springer US
• ISSN：1608-3393

文摘

2-(Allylamino)- and 2-(propargylamino)pyrido[2,3-d]pyrimidin-4(3H)-ones underwent intramolecular cyclization on heating in polyphosphoric acid to give angularly fused imidazo[1,2-a]pyrido[3,2-e]pyrimidin-5-ones. The cyclization of 2-(cinnamylamino)pyrido[2,3-d]pyrimidin-4(3H)-one under analogous conditions afforded linearly fused 4-phenyl-1,2,3,4-tetrahydro-6H-pyrido[2,3-d]pyrimido[1,2-a]pyrimidin-6-one. 2-(Allylamino)pyrido[2,3-d]pyrimidin-4(3H)-one reacted with iodine yielding 9-(iodomethyl)-8,9-dihydroimidazo[1,2-a]pyrido[3,2-e]pyrimidin-5(7H)-one as the major product, 2-(propargylamino)pyrido[2,3-d]pyrimidin-4(3H)-one gave rise to iodine addition product to the triple bond, and angularly fused 9-iodo-10-phenyl-7,8,9,10-tetrahydro-5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one was obtained from the 2-(cinnamylamino) derivative. Electrophilic cyclization of 2-(allylamino)- and 2-(cinnamylamino)pyrido[2,3-d]pyrimidin-4(3H)-ones by the action of phenylsulfanyl chloride led to the formation of angularly fused 9-(phenylsulfanylmethyl)-8,9-dihydroimidazo[1,2-a]pyrido[3,2-e]pyrimidin-5(7H)-one and 10-phenyl-9-phenylsulfanyl-7,8,9,10-tetrahydro-5H-pyrido[3,2-e]pyrimido[1,2-a]pyrimidin-5-one.