Facile synthesis of benzothiazoles via cascade reactions of 2-iodoanilines, acid chlorides and Lawesson's reagent.
In the presence of Lawesson's reagent, metal-free one-pot cascade reactions of 2-iodoanilines with acid chlorides proceeded smoothly leading to 2-substituted benzothiazoles in good to excellent yields under mild conditions. Three steps were involved in the reaction process: (1) 2-iodoanilines reacted with acid chlorides to afford benzamides, (2) benzamides transferred to benzothioamides in the presence of Lawesson's reagent, and (3) intramolecular cyclization of benzothioamides generated the expected benzothiazoles.
Ding
Qiuping
Q
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.
Huang
Xi-Gen
XG
Wu
Jie
J
D000814:Aniline Compounds / Q000737:chemistry*; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D015394:Molecular Structure; D009946:Organothiophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000814:Aniline Compounds; D052160:Benzothiazoles; D002712:Chlorides; D009946:Organothiophosphorus Compounds; C029887:2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide