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• W2175872568 endingPage "232" @default.
• W2175872568 startingPage "227" @default.
• W2175872568 abstract "A new, efficient, and straightforward synthesis of 3-arylmethyl-4-chloromethyl-2-imino-1,3-thiazolidines and 2-(N-acylimino)-3-arylmethyl-4-chloromethyl-1,3-thiazolidines has been developed by ring transformation of 1-arylmethyl-2-(thiocyanomethyl)aziridines upon treatment with a catalytic amount of titanium(IV) chloride in dichloromethane. The latter 2-(thiocyanomethyl)aziridines were prepared in high yields from 1-arylmethyl-2-(bromomethyl)aziridines by reaction with potassium thiocyanate in DMF. The 2-imino-1,3-thiazolidines and 2-(N-acylimino)-1,3-thiazolidines thus obtained can be easily interconverted, either by treatment with an acid chloride and a base in ether toward 2-(N-acylimino)thiazolidines or by treatment with potassium carbonate in methanol toward N-deprotected 2-iminothiazolidines. Dehydrohalogenation of 2-(N-acylimino)-3-arylmethyl-4-chloromethyl-1,3-thiazolidines by means of potassium tert-butoxide in DMSO afforded 2-(N-acylimino)-4-methyl-2,3-dihydro-1,3-thiazolines in good yields." @default.
• W2175872568 created "2016-06-24" @default.
• W2175872568 creator A5020239155 @default.
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• W2175872568 date "2004-12-10" @default.
• W2175872568 modified "2023-10-04" @default.
• W2175872568 title "A Novel Entry toward 2-Imino-1,3-thiazolidines and 2-Imino-1,3-thiazolines by Ring Transformation of 2-(Thiocyanomethyl)aziridines" @default.
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• W2175872568 doi "https://doi.org/10.1021/jo048486f" @default.
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