Premium
Photochemical Reactivity of 2‐Azido‐1,3‐thiazole and 2‐Azido‐1,3‐benzothiazole: A Procedure for the Aziridination of Enol Ethers
Author(s) -
D'Auria Maurizio,
Racioppi Rocco,
Viggiani Licia,
Zanirato Paolo
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800959
Subject(s) - chemistry , benzothiazole , thiazole , tautomer , enol , nitrene , medicinal chemistry , tetrazole , diastereomer , double bond , reactivity (psychology) , methyl acrylate , photochemistry , organic chemistry , polymer , copolymer , catalysis , medicine , alternative medicine , pathology
Direct irradiation of a mixture of the azido–tetrazole tautomers of 2‐azido‐1,3‐thiazole and 2‐azido‐1,3‐benzothiazole in toluene solution gives products arising from the intermediate nitrene, which in turn undergoes ring opening in the case of 2‐azido‐1,3‐thiazole to give a polymer, and dimerization in the case of 2‐azido‐1,3‐benzothiazole to give [1,3]benzothiazolo[2′,3′:3,4][1,2,4,5]tetraazino[6,1 b ][1,3]benzothiazolein low yields. When irradiation is performed in the presence of methyl acrylate or various enol ethers, aziridination of the double bond is observed, with good yields in the case of enol ethers. Among these, 1‐(6‐methyl‐3,4‐dihydro‐2 H ‐pyran‐2‐yl)ethanone undergoes aziridination with complete diastereoselectivity to give the (1 RS ,3 RS ,6 SR ) diastereomer.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)