Concise Access to 2-Aroylbenzothiazoles by Redox Condensation Reaction between o-Halonitrobenzenes, Acetophenones, and Elemental Sulfur.
A wide range of 2-aroylbenzothiazoles 3 including some pharmacologically relevant derivatives can be obtained in high yields by simply heating o-halonitrobenzenes 1, acetophenones 2, elemental sulfur, and N-methylmorpholine. This three-component nitro methyl coupling was found to occur in an excellent atom-, step-, and redox-efficient manner in which elemental sulfur played the role of nucleophile building block and redox moderating agent to fulfill electronic requirements of the global reaction.
Institut de Chimie des Substances Naturelles, CNRS-ICSN UPR 2301, Université Paris-Sud, 1 avenue de la Terrase, Gif-sur-Yvette 91198 Cedex, France.
Thanh Binh
TB
Nguyen
Institut de Chimie des Substances Naturelles, CNRS-ICSN UPR 2301, Université Paris-Sud, 1 avenue de la Terrase, Gif-sur-Yvette 91198 Cedex, France.
Karine
K
Pasturaud
Institut de Chimie des Substances Naturelles, CNRS-ICSN UPR 2301, Université Paris-Sud, 1 avenue de la Terrase, Gif-sur-Yvette 91198 Cedex, France.
Ludmila
L
Ermolenko
Institut de Chimie des Substances Naturelles, CNRS-ICSN UPR 2301, Université Paris-Sud, 1 avenue de la Terrase, Gif-sur-Yvette 91198 Cedex, France.
Ali
A
Al-Mourabit
D000098:Acetophenones / Q000737:chemistry*; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry; D009578:Nitrobenzenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D013455:Sulfur / Q000737:chemistry*
D000098:Acetophenones; D052160:Benzothiazoles; D009025:Morpholines; D009578:Nitrobenzenes; C038816:4-methylmorpholine; D013455:Sulfur