Synthesis, Table of Contents Synthesis 2019; 51(22): 4205-4214DOI: 10.1055/s-0039-1690616 paper © Georg Thieme Verlag Stuttgart · New York Acid-Catalyzed Condensation of o-Phenylenediammines and o-Aminophenols with α-Oxodithioesters: A Divergent and Regioselective Synthesis of 2-Methylthio-3-aryl/Heteroarylquinoxalines and 2-Acylbenzoxazoles Kuppalli R Kiran a Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570 006, India Email: rangappaks@gmail.com Email: mpsadashiva@gmail.com , Toreshettahally R Swaroop ∗ b Department of Studies in Organic Chemistry, University of Mysore, Manasagangothri, Mysuru, 570 006, India Email: swarooptr@gmail.com , Kodipura P Sukrutha a Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570 006, India Email: rangappaks@gmail.com Email: mpsadashiva@gmail.com , Jeegundipattana B Shruthi a Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570 006, India Email: rangappaks@gmail.com Email: mpsadashiva@gmail.com , Seegehally M Anil a Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570 006, India Email: rangappaks@gmail.com Email: mpsadashiva@gmail.com , Kanchugarakoppal S Rangappa∗ a Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570 006, India Email: rangappaks@gmail.com Email: mpsadashiva@gmail.com , Maralinganadoddi P Sadashiva ∗ a Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570 006, India Email: rangappaks@gmail.com Email: mpsadashiva@gmail.com › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract o-Phenylenediammines and o-aminophenols were reacted with α-oxodithioesters in a highly regioselective fashion to give 2-methylthio-3-aryl/heteroarylquinoxalines and 2-acylbenzoxazoles in 55–94% and 45–86%, respectively, in the presence of p-toluene sulfonic acid catalyst. Control experiments involving reaction of aniline with a α-oxodithioester indicated that the thiocarbonyl group is more reactive than the carbonyl group. Based on this, probable mechanisms for the formation of quinoxalines and benzoxazoles are given. Biological targets of the quinoxalines and benzoxazoles were identified by bioinformatics. It was found that quinoxalines have good binding affinity with human dual-specificity tyrosine-phosphorylation-regulated kinase 1A and benzoxazoles with human carboxylesterase. Key words Key wordsα-oxodithioester - quinoxaline - benzoxazole - condensation - p-TSA Full Text References References 1a Seitz LE, Suling WJ, Reynolds RC. J. Med. Chem. 2002; 45: 5604 1b Gazit A, App H, McMahon G, Chen J, Levitzki A, Bohmer FD. J. Med. Chem. 1996; 3: 2170 1c Monge A, Palop JA, Del Castillo JC, Caldero JM, Roca J, Romero G, Del Rio J, Lasheras B. J. Med. 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