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2-Amino-1,3-benzothiazole: Endo N-Alkylation with α-Iodo Methyl Ketones Followed by Cyclization.
| Content Provider | Europe PMC |
|---|---|
| Author | Dorofeev, Ivan A. Zhilitskaya, Larisa V. Yarosh, Nina O. Shainyan, Bagrat A. |
| Editor | Geronikaki, Athina Bunce, Richard A. |
| Copyright Year | 2023 |
| 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. |
| Journal | Molecules |
| Volume Number | 28 |
| DOI | 10.3390/molecules28052093 |
| PubMed Central reference number | PMC10004639 |
| Issue Number | 5 |
| PubMed reference number | 36903340 |
| e-ISSN | 14203049 |
| Language | English |
| Publisher | Molecular Diversity Preservation International (MDPI) |
| Publisher Date | 2023-02-23 |
| Access Restriction | Open |
| Subject Keyword | 2-amino-1,3-benzothiazole iodoacetone 1,3-diiodoacetone aromatic heteroaromatic α-iodo methyl ketones N-alkylation intramolecular cyclization iodide and triiodide salts |
| Content Type | Text |
| Resource Type | Article |
| Subject | Physical and Theoretical Chemistry Medicine Chemistry Drug Discovery Pharmaceutical Science Analytical Chemistry Molecular Medicine Organic Chemistry |
