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

Standard

Rh(II)-catalyzed and non-catalytic synthesis of (Z)-ethene-1,2-diamines from 1-tosyl-1,2,3-triazoles and primary anilines. / Васильченко, Дмитрий Сергеевич; Новиков, Михаил Сергеевич ; Ростовский, Николай Витальевич.

в: Chemistry of Heterocyclic Compounds, Том 59, № 9/10, 14.11.2023, стр. 666-671.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{b88efcda502f4bf7afb52f80322aeae3,

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

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. ",

author = "Васильченко, {Дмитрий Сергеевич} and Новиков, {Михаил Сергеевич} and Ростовский, {Николай Витальевич}",

year = "2023",

month = nov,

day = "14",

doi = "10.1007/s10593-023-03252-5",

language = "English",

volume = "59",

pages = "666--671",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer Nature",

number = "9/10",

}

RIS

TY - JOUR

T1 - Rh(II)-catalyzed and non-catalytic synthesis of (Z)-ethene-1,2-diamines from 1-tosyl-1,2,3-triazoles and primary anilines

AU - Васильченко, Дмитрий Сергеевич

AU - Новиков, Михаил Сергеевич

AU - Ростовский, Николай Витальевич

PY - 2023/11/14

Y1 - 2023/11/14

N2 - 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.

AB - 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.

UR - https://link.springer.com/article/10.1007/s10593-023-03252-5

UR - https://www.mendeley.com/catalogue/9c7e1988-7d49-3dac-8b64-e5fc88d9a77c/

U2 - 10.1007/s10593-023-03252-5

DO - 10.1007/s10593-023-03252-5

M3 - Article

VL - 59

SP - 666

EP - 671

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 9/10

ER -

ID: 114011055