Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Azirine-triazole hybrids : selective synthesis of 5-(2H-azirin-2-yl)-, 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines. / Krivolapova, Yulia V.; Tomashenko, Olesya A.; Funt, Liya D.; Spiridonova, Dar'ya V.; Novikov, Mikhail S.; Khlebnikov, Alexander F.
в: Organic and Biomolecular Chemistry, Том 20, № 27, 23.06.2022, стр. 5434-5443.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Azirine-triazole hybrids
T2 - selective synthesis of 5-(2H-azirin-2-yl)-, 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines
AU - Krivolapova, Yulia V.
AU - Tomashenko, Olesya A.
AU - Funt, Liya D.
AU - Spiridonova, Dar'ya V.
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F.
N1 - Publisher Copyright: © 2022 The Royal Society of Chemistry
PY - 2022/6/23
Y1 - 2022/6/23
N2 - Azirine-triazole hybrids, 1-R-5-(3-aryl-2H-azirin-2-yl)-1H-1,2,3-triazoles, were selectively synthesized by reaction of 1-(3-aryl-2H-azirin-2-yl)-2-(triphenylphosphoranylidene)ethanones with tosyl and (E)-2-benzoylvinyl azides in high yields at rt. The reaction with 2-azidopyridine makes it possible to obtain azirine-triazole-pyridine hybrids, albeit in moderate yields, at 170 °C. The mechanism and selectivity of the reaction of α-carbonylphosphoranes with azides are discussed on the basis of DFT calculations. According to the calculation, the reaction of α-carbonylphosphoranes with model mesyl azide, leading to 1,5-disubstituted triazoles proceeds via a non-concerted cycloaddition, while the reaction leading to 1,4-disubstituted triazoles proceeds via a concerted azide cycloaddition, but through the transition state which has much higher energy. In contrast to the reaction of α-(triphenylphosphoranylidene)ketones with TsN3, the reaction with TfN3 yields the α-diazo ketones. Ni-Catalyzed reaction of azirinyl-1,2,3-triazoles with acetylacetone provides pyrrole-triazole and pyrrole-triazole-pyridine hybrids in good yields under mild conditions.
AB - Azirine-triazole hybrids, 1-R-5-(3-aryl-2H-azirin-2-yl)-1H-1,2,3-triazoles, were selectively synthesized by reaction of 1-(3-aryl-2H-azirin-2-yl)-2-(triphenylphosphoranylidene)ethanones with tosyl and (E)-2-benzoylvinyl azides in high yields at rt. The reaction with 2-azidopyridine makes it possible to obtain azirine-triazole-pyridine hybrids, albeit in moderate yields, at 170 °C. The mechanism and selectivity of the reaction of α-carbonylphosphoranes with azides are discussed on the basis of DFT calculations. According to the calculation, the reaction of α-carbonylphosphoranes with model mesyl azide, leading to 1,5-disubstituted triazoles proceeds via a non-concerted cycloaddition, while the reaction leading to 1,4-disubstituted triazoles proceeds via a concerted azide cycloaddition, but through the transition state which has much higher energy. In contrast to the reaction of α-(triphenylphosphoranylidene)ketones with TsN3, the reaction with TfN3 yields the α-diazo ketones. Ni-Catalyzed reaction of azirinyl-1,2,3-triazoles with acetylacetone provides pyrrole-triazole and pyrrole-triazole-pyridine hybrids in good yields under mild conditions.
KW - Azides
KW - Azirines
KW - Ketones
KW - Pyridines
KW - Pyrroles
KW - Triazoles
UR - http://www.scopus.com/inward/record.url?scp=85133634861&partnerID=8YFLogxK
UR - https://www.mendeley.com/catalogue/2333b1e2-a5a8-3011-abaf-e98530b88744/
U2 - 10.1039/d2ob00908k
DO - 10.1039/d2ob00908k
M3 - Article
C2 - 35766322
AN - SCOPUS:85133634861
VL - 20
SP - 5434
EP - 5443
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 27
ER -
ID: 97334155