3-dialkylamino-1,2,4-triazoles via ZnII-catalyzed acyl hydrazide-dialkylcyanamide coupling

Standard

3-dialkylamino-1,2,4-triazoles via Zn^II-catalyzed acyl hydrazide-dialkylcyanamide coupling. / Yunusova, Sevilya N.; Bolotin, Dmitrii S.; Suslonov, Vitalii V.; Vovk, Mikhail A.; Tolstoy, Peter M.; Kukushkin, Vadim Yu.

в: ACS Omega, Том 3, № 7, 03.07.2018, стр. 7224-7234.

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

BibTeX

@article{ebbd0e68506944ecb3110fd308aab5d7,

title = "3-dialkylamino-1,2,4-triazoles via ZnII-catalyzed acyl hydrazide-dialkylcyanamide coupling",

abstract = "Zinc(II)-catalyzed (10 mol % ZnCl2) coupling of acyl hydrazides and dialkylcyanamides in ethanol leads to 3-dialkylamino-1,2,4-triazoles (76-99%; 17 examples). This reaction represents a novel, straightforward, and high-yielding approach to practically important 3-NR2-1,2,4-triazoles, which utilizes commercially available and/or easily generated substrates. Seventeen new 3-NR2-1,2,4-triazoles were characterized by HRESI+-MS and IR, 1H, and 13C{1H} NMR spectroscopies and five species additionally by single-crystal X-ray diffraction (XRD). The ZnII-catalyzed reaction proceeds via initial generation of the [Zn{RC({\^a}•O)NHNH2}3](ZnCl4) complexes (exemplified by isolation of the complex with R = Ph, 76%; characterized by HRESI+-MS, IR, CP-MAS TOSS 13C{1H} NMR, and XRD). Electronic effects of substituents at the acyl hydrazide moiety do not significantly affect the reaction rate and the yield of the target triazoles, whereas the steric hindrances reduce the reaction rate without affecting the yield of the heterocycles.",

keywords = "1,2,4-TRIAZOLE DERIVATIVES, AQUEOUS-MEDIA, BIOLOGICAL EVALUATION, BOND LENGTHS, CARBON-DIOXIDE, COORDINATION POLYMERS, COPPER CORROSION, METAL-ORGANIC FRAMEWORKS, NEUTRON-DIFFRACTION, ONE-POT SYNTHESIS",

author = "Yunusova, {Sevilya N.} and Bolotin, {Dmitrii S.} and Suslonov, {Vitalii V.} and Vovk, {Mikhail A.} and Tolstoy, {Peter M.} and Kukushkin, {Vadim Yu}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = jul,

day = "3",

doi = "10.1021/acsomega.8b01047",

language = "English",

volume = "3",

pages = "7224--7234",

journal = "ACS Omega",

issn = "2470-1343",

publisher = "American Chemical Society",

number = "7",

}

RIS

TY - JOUR

T1 - 3-dialkylamino-1,2,4-triazoles via ZnII-catalyzed acyl hydrazide-dialkylcyanamide coupling

AU - Yunusova, Sevilya N.

AU - Bolotin, Dmitrii S.

AU - Suslonov, Vitalii V.

AU - Vovk, Mikhail A.

AU - Tolstoy, Peter M.

AU - Kukushkin, Vadim Yu

PY - 2018/7/3

Y1 - 2018/7/3

N2 - Zinc(II)-catalyzed (10 mol % ZnCl2) coupling of acyl hydrazides and dialkylcyanamides in ethanol leads to 3-dialkylamino-1,2,4-triazoles (76-99%; 17 examples). This reaction represents a novel, straightforward, and high-yielding approach to practically important 3-NR2-1,2,4-triazoles, which utilizes commercially available and/or easily generated substrates. Seventeen new 3-NR2-1,2,4-triazoles were characterized by HRESI+-MS and IR, 1H, and 13C{1H} NMR spectroscopies and five species additionally by single-crystal X-ray diffraction (XRD). The ZnII-catalyzed reaction proceeds via initial generation of the [Zn{RC(â•O)NHNH2}3](ZnCl4) complexes (exemplified by isolation of the complex with R = Ph, 76%; characterized by HRESI+-MS, IR, CP-MAS TOSS 13C{1H} NMR, and XRD). Electronic effects of substituents at the acyl hydrazide moiety do not significantly affect the reaction rate and the yield of the target triazoles, whereas the steric hindrances reduce the reaction rate without affecting the yield of the heterocycles.

AB - Zinc(II)-catalyzed (10 mol % ZnCl2) coupling of acyl hydrazides and dialkylcyanamides in ethanol leads to 3-dialkylamino-1,2,4-triazoles (76-99%; 17 examples). This reaction represents a novel, straightforward, and high-yielding approach to practically important 3-NR2-1,2,4-triazoles, which utilizes commercially available and/or easily generated substrates. Seventeen new 3-NR2-1,2,4-triazoles were characterized by HRESI+-MS and IR, 1H, and 13C{1H} NMR spectroscopies and five species additionally by single-crystal X-ray diffraction (XRD). The ZnII-catalyzed reaction proceeds via initial generation of the [Zn{RC(â•O)NHNH2}3](ZnCl4) complexes (exemplified by isolation of the complex with R = Ph, 76%; characterized by HRESI+-MS, IR, CP-MAS TOSS 13C{1H} NMR, and XRD). Electronic effects of substituents at the acyl hydrazide moiety do not significantly affect the reaction rate and the yield of the target triazoles, whereas the steric hindrances reduce the reaction rate without affecting the yield of the heterocycles.

KW - 1,2,4-TRIAZOLE DERIVATIVES

KW - AQUEOUS-MEDIA

KW - BIOLOGICAL EVALUATION

KW - BOND LENGTHS

KW - CARBON-DIOXIDE

KW - COORDINATION POLYMERS

KW - COPPER CORROSION

KW - METAL-ORGANIC FRAMEWORKS

KW - NEUTRON-DIFFRACTION

KW - ONE-POT SYNTHESIS

UR - http://www.scopus.com/inward/record.url?scp=85059615119&partnerID=8YFLogxK

U2 - 10.1021/acsomega.8b01047

DO - 10.1021/acsomega.8b01047

M3 - Article

AN - SCOPUS:85059615119

VL - 3

SP - 7224

EP - 7234

JO - ACS Omega

JF - ACS Omega

SN - 2470-1343

IS - 7

ER -

ID: 35115355