Facile synthesis of quinoxaline-2-thiol and quinoxaline from α-oxo sulfines and o-aryl diamines

Synthesis ◽  
2022 ◽  
Jun Dong ◽  
Youwei Chen ◽  
Xingcai Huang

A series of quinoxaline-2-thiol and quinoxaline were prepared in moderate to good yields from various phenacyl sulfoxides bearing 1-methyl-1H-tetrazole and o-aryl diamines. The proposed reaction mechanism involves generation of sulfines from the phenacyl sulfoxides bearing 1-methyl-1H-tetrazole through thermolysis elimination. Then, site-selectively carbophilic addition of sulfines by o-aryl diamines, followed by elimination, intramolecular nucleophilic addition and dehydration condensation. The current method provides a direct and simple strategy for the preparation of quinoxaline-2-thiols and quinoxalines.

2010 ◽  
Vol 12 (23) ◽  
pp. 5494-5497 ◽  
Santos Fustero ◽  
Javier Moscardó ◽  
María Sánchez-Roselló ◽  
Elsa Rodríguez ◽  
Pablo Barrio

Synthesis ◽  
2008 ◽  
Vol 2008 (20) ◽  
pp. 3319-3325
Margaret Brimble ◽  
Daryl Crimmins ◽  
Ivaylo Dimitrov ◽  
Patrick O’Connor ◽  
Vittorio Caprio

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7212
Hasil Aman ◽  
Yu-Chiao Huang ◽  
Yu-Hao Liu ◽  
Yu-Lin Tsai ◽  
Min Kim ◽  

A novel synthetic pathway to approach 3-(imino)isoindolin-1-ones by the Co-catalyzed cyclization reaction of 2-bromobenzamides with carbodiimides has been developed. This catalytic reaction can tolerate a variety of substituents and provide corresponding products in moderate yields for most cases. According to the literature, the reaction mechanism is proposed through the formation of a five-membered aza-cobalacycle complex, which carries out the following reaction subsequence, including nucleophilic addition and substitution, to furnish the desired structures.

2007 ◽  
Vol 2007 (8) ◽  
pp. 439-441 ◽  
Ashraf A. Aly ◽  
Ahmed M. NourEl-Din ◽  
Moshen A.-M. Gomaa ◽  
Alan B. Brown ◽  
Magda S. Fahmi

2,3-Diphenylcyclopropenone (1) reacts with N-imidoylthioureas 2a–e to form the pyrimidin-4(3 H)-ones 5a–e. The reaction mechanism can be described as due to stepwise addition accompanied by elimination of phenyl isothiocyanate.

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