Selective synthesis of pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl) formamide, or N-(1H-pyrazol-5-yl)formamidine derivatives from N-1-substituted-5-aminopyrazoles with new Vilsmeier-type reagents

Chun Hsi Chang, Henry J. Tsai, Yu Ying Huang, Hui Yi Lin, Li Ya Wang, Tian Shung Wu, Fung Fuh Wong

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Various halomethyleniminium salts as novel Vilsmeier agents were synthesized from formamide or N-methylformamide with POCl3. Treatment of N-1-substituted-aminopyrazoles including N-1-phenyl-5-aminopyrazoles, N-1-(2-pyridinyl)-5-aminopyrazoles, and N-1-(2-quinolinyl)-5-aminopyrazoles with these agents gave the corresponding pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl)formamide, or N-(1H-pyrazol-5-yl)formamidine. The reaction was different from the traditional Vilsmeier-type reaction and the plausible reactive pathways were proposed for the unexpected result.

Original languageEnglish
Pages (from-to)1378-1386
Number of pages9
JournalTetrahedron
Volume69
Issue number4
DOIs
Publication statusPublished - 2013 Jan 28

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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