Electrophilic cyclization of N-allyl(propargyl)-5-amino-1H-pyrazole-4-carboxamides. Synthesis of 4-[(dihydro)oxazol-2-yl]-1H-pyrazol-5-amines

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• 作者：N. A. Bondarenko ; A. I. Vas’kevich ; A. V. Bol’but…
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2015
• 出版时间：December 2015
• 年：2015
• 卷：51
• 期：12
• 页码：1774-1783
• 全文大小：343 KB
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• 作者单位：N. A. Bondarenko (1) (2)
  A. I. Vas’kevich (1) (2)
  A. V. Bol’but (1)
  E. B. Rusanov (1)
  M. V. Vovk (1)
  
  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02094, Ukraine
  2. “Kyiv Polytechnic Institute” National Technical University of Ukraine, pr. Pobedy 37, Kiev, 03056, Ukraine
  
• 刊物主题：Organic Chemistry;
• 出版者：Springer US
• ISSN：1608-3393

文摘

N-Allyl-5-amino-1H-pyrazole-4-carboxamides in reactions with polyphosphoric acid, with N-halosuccinimides in chloroform, and with (chlorosulfanyl)benzenes in nitromethane in the presence of lithium perchlorate underwent cyclization involving the N-allylamide fragment to give 4-[5-methyl(halomethyl)-4,5-dihydrooxazol-2-yl]-1H-pyrazol-5-amines and 2-(5-amino-1H-pyrazol-4-yl)-5-[(arylsulfanyl)methyl]-4,5-dihydro-1,3-oxazolium perchlorates, respectively. Analogous reactions of N-propargyl-5-amino-1H-pyrazole-4-carboxamides with polyphosphoric acid afforded 4-(5-methyloxazol-2-yl)-1H-pyrazol-5-amines, and with (chlorosulfanyl) benzenes, 2-(5-amino-1H-pyrazol-4-yl)-5-[(arylsulfanyl)methylidene]-4,5-dihydro-1,3-oxazolium perchlorates. Original Russian Text © N.A. Bondarenko, A.I. Vas’kevich, A.V. Bol’but, E.B. Rusanov, M.V. Vovk, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 12, pp. 1807–1816.