Premium
Methyl ( E )‐2‐(1‐Aryl‐4,5‐dihydro‐1 H ‐tetrazol‐5‐ylidene)‐2‐cyanoacetate from Methyl 3,3‐Diazido‐2‐cyanoacrylate and Primary Aromatic Amines
Author(s) -
Saalfrank Rolf W.,
Fischer Michael,
Wirth Uwe,
Zimmermann Helmuth
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198711601
Subject(s) - chemistry , nitrene , ring (chemistry) , aryl , substituent , medicinal chemistry , azide , organic chemistry , catalysis , alkyl
A 1,5′ ring closure to give 3 and N 2 elimination accompanied by nitrene addition to the CC bond to give 4 –these are the reaction possibilities available to vinyl azides 2 if the substituent at the 4 position is an NHR′ group that can become involved in the reaction. Previously, only 1,5 and 3,5 ring‐closure reactions were known for vinyl azides substituted at the 4 position with donor groups. The azides 4 are easily prepared from the methyl cyanoacrylate 1 and primary aryl amines.