Rh(II)-catalyzed and non-catalytic synthesis of (Z)-ethene-1,2-diamines from 1-tosyl-1,2,3-triazoles and primary anilines

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-1 H -1,2,3-triazole with 2-bromo-4-ni...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2023-09, Vol.59 (9-10), p.666-671
Main Authors: Vasilchenko, Dmitrii S., Novikov, Mikhail S., Rostovskii, Nikolai V.
Format: Article
Language:English
Subjects:
Aniline
Aromatic compounds
Chemical synthesis
Chemistry
Chemistry and Materials Science
Diamines
Ethylene
Hydrogen bonds
Organic Chemistry
Pharmacy
Substrates
Triazoles
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Summary: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-1 H -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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-023-03252-5