In:
Synthesis, Georg Thieme Verlag KG, Vol. 53, No. 11 ( 2021-06), p. 1901-1910
Abstract:
A divergent efficient assembly of disubstituted 1,2,4-triazoles was established by cyclization of readily accessible N′-nitro-2-hydrocarbylidene-hydrazinecarboximidamides with moderate to excellent yields under mild reaction conditions. This divergent synthetic strategy was achieved simply by varying the reaction conditions. Under acidic conditions, amino-1,2,4-triazoles were obtained by an intramolecular redox reaction involving the NO2 group. Control experiments and DFT studies revealed that this transformation proceeds via an intramolecular 1,3-hydride transfer pathway leading to HNO2 elimination. Under neutral conditions with water as the solvent, nitroimino-1,2,4-triazoles were obtained by oxidative intramolecular annulation under air.
Type of Medium:
Online Resource
ISSN:
0039-7881
,
1437-210X
Language:
English
Publisher:
Georg Thieme Verlag KG
Publication Date:
2021
detail.hit.zdb_id:
204080-3
detail.hit.zdb_id:
2033062-5
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