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Synthesis of 2-(2-R1-Hydrazino)-5-(R2-benzyl)-2-thiazolines on the Basis of Meerweins Arylation Products of Allyl Isothiocyanate

Author(s): Volodymyr V. Karpyak | Mykola D. Obushak | Mykola I. Ganushchak

Journal: Molecules ISSN 1420-3049
Volume: 8; Issue: 2; Start page: 263; Date: 2003;
Original page

Keywords: Arylation | allyl isothiocyanate | thiosemicarbazides | 2-thiazolines | cyclizations

ABSTRACT
3-Aryl-2-chloropropylisothiocyanates (1) are formed by interaction of arenediazonium chlorides with allyl isothiocyanate. Adducts 1 react with monoacylhydrazines to form 1-acyl-4-(3-aryl-2-chloropropyl)thiosemicarbazides (2a–d). Thiosemicarbazides 2a–d in the presence of bases selectively transform into 2-(2-R1-hydrazino)-5-(R2-benzyl)-2-thiazolines (3a–d).