Hydrazine in the Ugi Tetrazole Reaction

Pravin Patil, Ji Zhang, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Alexander Dömling*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

16 Citations (Scopus)

Abstract

We describe the hitherto unknown use of N-Boc-protected hydrazine in the Ugi tetrazole reaction to access a library of highly substituted 5-(hydrazinomethyl)-1-methyl-1H-tetrazoles. The reaction is very versatile and good to high yielding. A one-pot, two-step procedure is given.
Original languageEnglish
Pages (from-to)1122-1130
Number of pages9
JournalSynthesis
Volume48
Issue number8
DOIs
Publication statusPublished - 15-Feb-2016

Keywords

  • hydrazine
  • isocyanides
  • multicomponent reaction
  • tetrazoles
  • Ugi reaction
  • benzyl 4 [2 (tert butoxycarbonyl)hydrazino] 4[1 [2 (1h indol 3 yl)ethyl] 1h tetrazol 5 yl]piperidine 1 carboxylic acid
  • hydrazine derivative
  • tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 2 methylpropyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 2 phenylethyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 3 methylbutyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl) 3 phenylpropyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [1 (1 benzyl 1h tetrazol 5 yl)(cyclohexyl)methyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [1 (1 phenethyl 1h tetrazol 5 yl)cyclohexyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [1 [1 benzyl 4 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]piperidin 4 yl]]hydrazine 1 carboxylic acid
  • tert butyl 2 [1 chloro 2 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]propan 2 yl]hydrazine 1 carboxylic acid
  • tert butyl 2 [2 [1 (1 methoxy 4 methyl 1 oxopentan 2 yl) 1h tetrazol 5 yl]propan 2 yl]hydrazine 1 carboxylic acid
  • tert butyl 2 [2 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]butan 2 yl]hydrazine 1 carboxylic acid
  • tert butyl 2 [2 chloro 1 [1 (4 chlorobenzyl) 1h tetrazol 5 yl]ethyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [2 methyl 1 (1 phenethyl 1h tetrazol 5 yl)propyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [3 methyl 1 (1 phenethyl 1h tetrazol 5 yl)butyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [cyclohexyl (1 phenethyl 1h tetrazol 5 yl)methyl]hydrazine 1 carboxylic acid
  • tert butyl 2 [cyclohexyl(1 cyclohexyl 1h tetrazol 5 yl)methyl]hydrazine 1 carboxylic acid
  • tert butyl 2[1 (1 tert butyl 1h tetrazol 5 yl) 3 phenylpropyl]hydrazine 1 carboxylic acid
  • unclassified drug
  • article
  • carbon nuclear magnetic resonance
  • chemical reaction
  • deprotection reaction
  • drug isolation
  • drug screening
  • electrospray mass spectrometry
  • mass spectrometry
  • one pot synthesis
  • proton nuclear magnetic resonance
  • proton transport
  • supercritical fluid chromatography
  • Ugi tetrazole reaction

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