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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.

In: Chemistry of Heterocyclic Compounds, Vol. 59, No. 9/10, 14.11.2023, p. 666-671.

Research output: Contribution to journal › Article › peer-review

Harvard

Васильченко, ДС, Новиков, МС & Ростовский, НВ 2023, 'Rh(II)-catalyzed and non-catalytic synthesis of (Z)-ethene-1,2-diamines from 1-tosyl-1,2,3-triazoles and primary anilines', Chemistry of Heterocyclic Compounds, vol. 59, no. 9/10, pp. 666-671. https://doi.org/10.1007/s10593-023-03252-5

APA

Васильченко, Д. С., Новиков, М. С., & Ростовский, Н. В. (2023). Rh(II)-catalyzed and non-catalytic synthesis of (Z)-ethene-1,2-diamines from 1-tosyl-1,2,3-triazoles and primary anilines. Chemistry of Heterocyclic Compounds, 59(9/10), 666-671. https://doi.org/10.1007/s10593-023-03252-5

Vancouver

Васильченко ДС, Новиков МС, Ростовский НВ. Rh(II)-catalyzed and non-catalytic synthesis of (Z)-ethene-1,2-diamines from 1-tosyl-1,2,3-triazoles and primary anilines. Chemistry of Heterocyclic Compounds. 2023 Nov 14;59(9/10):666-671. https://doi.org/10.1007/s10593-023-03252-5

Author

Васильченко, Дмитрий Сергеевич ; Новиков, Михаил Сергеевич ; Ростовский, Николай Витальевич. / Rh(II)-catalyzed and non-catalytic synthesis of (Z)-ethene-1,2-diamines from 1-tosyl-1,2,3-triazoles and primary anilines. In: Chemistry of Heterocyclic Compounds. 2023 ; Vol. 59, No. 9/10. pp. 666-671.

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