328119-58-0Relevant academic research and scientific papers
2H-Azirines as dipolarophiles
Pinho E Melo, Teresa M. V. D.,Cardoso, Ana L.,Gomes, Clara S. B.,Rocha Gonsalves, Anto?nio M. D'A.
, p. 6313 - 6315 (2003)
2H-Azirine-3-carboxylates unsubstituted at C-2 act as dipolarophiles in the reaction with diazomethane giving new 4,5-dihydro-3H-pyrazole derivatives. The synthesis of a pyrimidine was also achieved via 1,3-dipolar cycloaddition of methyl 2-bromo-3-phenyl
Enantioselective Reaction of 2 H-Azirines with Oxazol-5-(4 H)-ones Catalyzed by Cinchona Alkaloid Sulfonamide Catalysts
Fujita, Kazuki,Miura, Masataka,Funahashi, Yasuhiro,Hatanaka, Tsubasa,Nakamura, Shuichi
supporting information, p. 2104 - 2108 (2021/04/05)
The enantioselective reaction of 2H-azirines with oxazol-5-(4H)-ones (oxazolones) using a cinchona alkaloid sulfonamide catalyst has been developed. The reaction proceeded at the C-2 position of oxazolones to afford products with consecutive tetrasubstitu
Catalytic Enantioselective Reaction of 2H-Azirines with Thiols Using Cinchona Alkaloid Sulfonamide Catalysts
Nakamura, Shuichi,Hayama, Daiki,Miura, Masataka,Hatanaka, Tsubasa,Funahashi, Yasuhiro
supporting information, p. 856 - 859 (2018/02/09)
The first catalytic enantioselective reaction of 2H-azirines with thiols has been developed. The obtained aziridines can be converted to optically active oxazolines, aziridylamides, or α-sulfonyl esters. Transformation of these optically active aziridines
Exploiting the chemistry of strained rings: Synthesis of indoles via domino reaction of aryl iodides with 2 H-azirines
Candito, David A.,Lautens, Mark
supporting information; experimental part, p. 3312 - 3315 (2010/10/19)
(Equation Presented). The highly strained 2H-azirine ring system has been the source of considerable theoretical and synthetic work. The reaction of these strained heterocycles with transition metals has been documented to give rise to ring opening and subsequent formation of varied heterocycles. An interesting domino reaction is described wherein the strained bicyclic alkene, norbornene, mediates the reaction of 2H-azirines with aryl iodides under palladium catalysis to provide indole or polycyclic dihydroimidazole heterocycles.
Formation of pyridin-4(1H)-one versus 1H-azepin-4(7H)-one by treatment of 4-tert-butyldimethylsilyloxy-2-amino-1-aza-bicyclo[4.1.0]hept-3-enes with tetrabutylammonium fluoride
Alves, M. José,Fortes, A. Gil,Costa, F. Teixeira,Duarte, Vera C.M.
, p. 11167 - 11173 (2008/02/13)
Cycloadducts 3 and 4 were treated with tetrabutylammonium fluoride and rapidly suffer cleavage on the three-membered ring to form either pyridin-4(1H)-one or 1H-azepin-4(7H)-one. When R1 is an oxycarbonyl or a 2-pyridyl group and R2
Improved procedure for cyclization of vinyl azides into 3-substituted-2H-azirines
Timén, ?sa Sj?holm,Risberg, Erik,Somfai, Peter
, p. 5339 - 5341 (2007/10/03)
A significantly improved procedure for the preparation of 3-substituted 2H-azirines has been developed. By cyclization of the corresponding vinyl azides in low boiling solvents in closed vessels at elevated temperature, high purity, short reaction time an
Addition of pyrimidine and purine bases to benzyl 2H-azirine-3-carboxylate
Gilchrist,Mendonca
, p. 1843 - 1845 (2007/10/03)
Benzyl 2H-azirine-3-carboxylate has been generated from benzyl acrylate in three steps. Thymine, uracil, adenine and other nucleobases add to the C = N bond of the azirine to give 2-substituted benzyl aziridine-2-carboxylates in moderate yield.
