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. 2023 Feb 23;28(5):2093.
doi: 10.3390/molecules28052093.

2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization

Ivan A Dorofeev  1 , Larisa V Zhilitskaya  1 , Nina O Yarosh  1 , Bagrat A Shainyan  1
Affiliations

2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization

Ivan A Dorofeev et al. Molecules. .

Abstract

Reactions of 2-amino-1,3-benzothiazole with aliphatic, aromatic and heteroaromatic α-iodoketones in the absence of bases or catalysts have been studied. The reaction proceeds by N-alkylation of the endocyclic nitrogen atom followed by intramolecular dehydrative cyclization. The regioselectivity is explained and the mechanism of the reaction is proposed. A number of new linear and cyclic iodide and triiodide benzothiazolium salts have been obtained and their structure proved by NMR and UV spectroscopy.

Keywords: 1,3-diiodoacetone; 2-amino-1,3-benzothiazole; N-alkylation; aromatic; heteroaromatic α-iodo methyl ketones; intramolecular cyclization; iodide and triiodide salts; iodoacetone.

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Conflict of interest statement

The authors declare no competing financial interests.

Figures

Scheme 1
Scheme 1
The reactions of 2-amino-1,3-benzothiazole 1 with α-iodoketones 2a–f.
Scheme 2
Scheme 2
The reactions of salts 3a–f with elemental iodine.
Scheme 3
Scheme 3
Cyclization of iodides 3a–f to 6a–f and conversion of the latter to triiodides 5a–f.
Scheme 4
Scheme 4
Reaction of 2-aminobenzothiazole 1 with 1,3-diiodoacetone 7.
See this image and copyright information in PMC

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