Rh(II)-CATALYZED AND NON-CATALYTIC SYNTHESIS OF (<i>Z</i>)-ETHENE-1,2-DIAMINES FROM 1-TOSYL-1,2,3-TRIAZOLES AND PRIMARY ANILINES

Authors

  • Дмитрий С. Васильченко Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Михаил С. Новиков Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Николай В. Ростовский Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

DOI:

https://doi.org/10.1007/7868

Keywords:

anilines, enediamines, carbenes, 1, 2, 3-triazoles, insertion into N–H bond, metallocatalysis

Abstract

The reactions of 4-aryl-1-tosyl-1,2,3-triazoles with substituted primary 2- or 4-nitroanilines, catalyzed by dirhodium tetrapivalate were used to synthesize stable (Z)-N-aryl-N'-tosylethene-1,2-diamines. The analogous reaction of 4-phthalimido-1-tosyl-1Н-1,2,3-triazole with 2-bromo-4-nitroaniline proceeded upon heating in the absence of catalyst, providing the first example for non-catalytic insertion of a carbene generated from 1-sulfonyl-1,2,3-triazole into an N–H bond. All ethene-1,2-diamines were isolated without resorting to chromatographic purification. The synthesized ethene-1,2-diamines contained two NH groups in a cis relationship and present interest as new bidentate ligands, as well as substrates for the synthesis of N,N-heterocycles.

Authors: Dmitrii S. Vasilchenko, Mikhail S. Novikov, Nikolai V. Rostovskii*

Author Biographies

Дмитрий С. Васильченко, Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

аспирант, инженер-исследователь кафедры органической химии

Михаил С. Новиков, Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

д.х.н., профессор кафедры органической химии

Николай В. Ростовский, Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

head of the department of organic chemistry

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Published

2023-11-01

Issue

Vol. 59 No. 9/10 (2023)

Section

Original Papers