Affiliation:
1. Institute of Physical and Organic Chemistry Southern Federal University 194/2 Stachki St. Rostov on Don 344090 Russian Federation
2. Department of Chemistry of the Institutes of Mathematics and Natural Sciences North Caucasus Federal University 1a Pushkina St. Stavropol 355009 Russian Federation
Abstract
AbstractThe S(O,N)‐benzyl ethers of N‐arylquinone imines undergo cyclization under the action of bases to form products of the benzothiazol, benzoxazole, and benzimidazole series, while under thermal conditions they undergo a non‐catalyzed rearrangement to form spiro‐cyclohexadiene derivatives of benzazines. The benzimidazole, spirobenzothiazine, and spirobenzoxazine structures were supported by the x‐ray diffraction method. The possibility of intramolecular photochemical cyclization was investigated; ortho‐S(O,N)‐benzyl‐substituted N‐arylquinone imines show high photostability under UV irradiation. The features of the cyclization processes of quinone imine derivatives were revealed by DFT calculations using the wB97XD/6‐311++G** method.
Funder
Ministry of Science and Higher Education of the Russian Federation
Cited by
1 articles.
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