{"title":"A Formal [3+3] Annulation of Morita–Baylis–Hillman Ketones to Construct Pyrimidobenzothiazoles","authors":"Rajkiran Kumari, Suman Kumawat, Easwar Srinivasan","doi":"10.1055/a-2373-0255","DOIUrl":null,"url":null,"abstract":"A calcium triflate promoted reaction of Morita–Baylis–Hillman (MBH) ketones, derived by the oxidation of MBH adducts, with 2-aminobenzothiazoles resulted in the formation of a 4H-pyrimido[2,1-b]benzothiazole. Formally, the transformation represents a [3+3] annulation and presumably proceeds via an aza-Michael addition followed by an intramolecular condensation. The reaction is completely regioselective and tolerates a wide range of substrates to afford a variety of analogs of the fused heterocycle in good yields.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"77 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2373-0255","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A calcium triflate promoted reaction of Morita–Baylis–Hillman (MBH) ketones, derived by the oxidation of MBH adducts, with 2-aminobenzothiazoles resulted in the formation of a 4H-pyrimido[2,1-b]benzothiazole. Formally, the transformation represents a [3+3] annulation and presumably proceeds via an aza-Michael addition followed by an intramolecular condensation. The reaction is completely regioselective and tolerates a wide range of substrates to afford a variety of analogs of the fused heterocycle in good yields.
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