1224507-79-2Relevant academic research and scientific papers
Copper-catalyzed synthesis of 2-aminobenzothiazoles from 2-iodophenyl isocyanides, potassium sulfide and amines
Min, Hao,Xiao, Genhua,Liu, Wenjuan,Liang, Yun
, p. 11088 - 11091 (2016/12/09)
A simple and practically useful synthetic method for the synthesis of a variety of 2-aminobenzothiazoles was developed. This methodology could construct one C-N bond and two C-S bonds in a step reaction and provide the desired products in good to perfect yields.
Cu(ii) catalysed chemoselective oxidative transformation of thiourea to thioamidoguanidine/2-aminobenzothiazole
Sahoo, Santosh K.,Khatun, Nilufa,Gogoi, Anupal,Deb, Arghya,Patel, Bhisma K.
, p. 438 - 446 (2013/04/10)
2-Haloaryl-sec-alkyl unsymmetrical thioureas (Tu) (halo = -F, -Cl) with a catalytic amount of Cu(ii) salt get oxidised in situ to their disulfide intermediates followed by an imine-disulfide rearrangement to give thioamidoguanidino (Tag) moieties at room temperature. During this process Cu(ii) gets reduced to Cu(i) and forms a complex with the Tag moiety from which Tag moiety can be isolated upon treatment with ammonia. However, when the same reaction was performed at an elevated temperature with a catalytic quantity of Cu(ii) salt, Tu bearing o-halogens (-F, -Cl) gave 2-aminobenzothiazoles via a dehalogenative heteroarylation path and not by the Hugerschoff path involving an electrophilic substitution reaction. For thioureas containing reactive ortho halogens (such as -Br, -I) the reaction proceeds at room temperature giving 2-aminobenzothiazoles via a dehalogenative path requiring a catalytic quantity of Cu(ii). No transformation of thiourea (Tu) to Tag was observed with Cu(i) salts suggesting the requirement of an oxidising Cu(ii) salt for this oxidative transformation. Mild reaction conditions, environmentally benign reagents and solvent, high yields, tolerance of various functional groups are some of the essential features of this methodology.
Metal-free synthesis of 2-substituted (N, O, C) Benzothiazoles via an intramolecular C-S bond formation
Feng, Enguang,Huang, He,Zhou, Yu,Ye, Deju,Jiang, Hualiang,Liu, Hong
experimental part, p. 422 - 429 (2010/09/05)
An efficient, economical, and convenient method was developed for the preparation of 2-substituted (N, O, C) benzothiazoles from N′-substituted- N-(2-halophenyl)thioureas, O′-substituted-N-(2-halophenyl) carbamothioates, or N-(2-halophenyl) thioamides via a base-promoted cyclization in dioxane without any transition metal. A one-pot variant combining the synthesis of the thiourea and the cyclization was also demonstrated. High yields were obtained, and a variety of functional groups were tolerated under these conditions. Transition-metal-free, mild reactive conditions, wide application scope, and shorter reaction times make this method superior to the reported methods for the synthesis of 2-substituted benzothiazoles and suitable for combinatorial format.
