76007-15-3Relevant academic research and scientific papers
Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y
Thierry, Thibault,Pfund, Emmanuel,Lequeux, Thierry
supporting information, p. 14826 - 14830 (2021/10/01)
A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.
Synthesis and Photolysis of Azido-benzothiophens, -benzothiazoles, -benzimidazoles, and -indazoles: Novel 6,7-diamino-benzothiazoles, -benzimidazoles, and -indazoles and 6-Diethylamino-8H-thiazoloazepines
Gallagher, Peter T.,Iddon, Brian,Suschitzky, Hans
, p. 2362 - 2370 (2007/10/02)
Irradiation of the 6-azidobenzothiazoles (4)-(9) (see Scheme) in the presence of an excess of a secondary amine gave either the corresponding 6,7-diaminobenzothiazole (14)-(20), a 6-amino-8H-thiazoloazepine (21)-(24), a mixture of both, or intractable material .Irradiation of 7-azido-3-methylbenzothiophen in an excess of diethylamine gave 7-amino-3-methylbenzothiophen and a trace of 3,3'-dimethyl-7,7'-azobenzothiophen. 6-Azidoindazole gave 7-amino-6-diethylaminoindazole (32) and 5(6)-azidobenzimidazole gave a mixture of 4(7)-amino- 5(6)-diethylaminobenzimidazole (33) and 5(6)-amino-4(7)-diethylaminobenzimidazole (34).Photolysis of either 6-azidobenzothiazole or its 2-methyl derivative in a methoxide-methanol-dioxan mixture gave the corresponding 6-methoxy-8H-thiazoloazepine, (30) or (31), respectively.
