Visible Light‐Mediated Coupling of Thioureas and 1, 3‐Dicarbonyls: Towards a Leaving Group‐Free Synthesis of Aminothiazoles. Issue 8 (22nd February 2018)

• Record Type: Journal Article
• Authors: Roslan, Irwan Iskandar; Ng, Kian‐Hong; Gondal, Mohammed Ashraf; Basheer, Chanbasha; Dastageer, Mohamed A.; Jaenicke, Stephan; Chuah, Gaik‐Khuan
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 8(2018)
• Page Start: 1584
• Page End: 1589
• Publication Date: 2018-02-22
• Subjects: Photocatalysis -- Radicals -- Green chemistry -- Heterocycles -- Cyclization; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201701565
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A synthesis of aminothiazoles from various 1, 3‐dicarbonyls and thioureas without a leaving group has been developed. The reaction is photocatalyzed by tetraiodofluorescein, an organic dye. Under irradiation with green LEDs, a sulfur radical is generated in situ from thiourea, followed by addition to the enol tautomer, forming the aminothiazole backbone. This novel strategy provides a greener alternative to the traditional leaving group protocols, with excellent atom economy. Abstract :