TY - JOUR

T1 - Methyl (1aRS,7aSR)-7-formyl-1a-phenyl-1,1a-dihydroazirino[2,3-b]benzo[e][1,4]thiazine-7a(7H)-carboxylate

AU - Филиппов, Илья Павлович

AU - Агафонова, Анастасия Викторовна

AU - Ростовский, Николай Витальевич

AU - Новиков, Михаил Сергеевич

PY - 2025/12/4

Y1 - 2025/12/4

N2 - The first representative of the aziridine-fused benzo[e][1,4]thiazine series was synthesized from methyl 2-bromo-2-phenyl-2H-azirine-2-carboxylate and benzo[d]thiazole in 74% yield. The reaction proceeds via the SN2′-SN2′-cascade to form the azirinylthiazolium salt followed by a water-induced thiazole ring expansion. The structure of the title compound was established based on 1H, 13C, 2D NMR spectroscopy and high-resolution mass spectrometry, and unambiguously confirmed by X-ray diffraction analysis.

AB - The first representative of the aziridine-fused benzo[e][1,4]thiazine series was synthesized from methyl 2-bromo-2-phenyl-2H-azirine-2-carboxylate and benzo[d]thiazole in 74% yield. The reaction proceeds via the SN2′-SN2′-cascade to form the azirinylthiazolium salt followed by a water-induced thiazole ring expansion. The structure of the title compound was established based on 1H, 13C, 2D NMR spectroscopy and high-resolution mass spectrometry, and unambiguously confirmed by X-ray diffraction analysis.

M3 - Letter

VL - 2025

JO - MolBank

JF - MolBank

SN - 1422-8599

IS - 4

M1 - M2101

ER -