Rationalization of Benzazole-2-carboxylate versus Benzazine-3-one/Benzazine-2,3-dione Selectivity Switch during Cyclocondensation of 2-Aminothiophenols/Phenols/Anilines with 1,2-Biselectrophiles in Aqueous Medium was written by Dhameliya, Tejas M.;Chourasiya, Sumit S.;Mishra, Eshan;Jadhavar, Pradeep S.;Bharatam, Prasad V.;Chakraborti, Asit K.. And the article was included in Journal of Organic Chemistry in 2017.Application of 1910-90-3 This article mentions the following:
The cyclocondensation reaction of 2-aminothiophenols with 1,2-biselectrophiles such as Et glyoxalate and di-Et oxalate in aqueous medium leads to the formation of benzothiazole-2-carboxylates via the 5-endo-trig process contrary to Baldwin’s rule. The reaction of 2-aminophenols/anilines produced the corresponding benzazine-3-ones or benzazine-2,3-diones via the 6-exo-trig process in compliance with Baldwin’s rule. The mechanistic insights of these cyclocondensation reactions using the hard-soft acid-base principle, quantum chem. calculations (d. functional theory), and orbital interaction studies rationalize the selectivity switch of benzothiazole-2-carboxylates vs. benzazine-3-ones/benzazine-2,3-diones. The presence of water facilitates these cyclocondensation reactions by lowering of the energy barrier. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3Application of 1910-90-3).
6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3) belongs to quinoxaline derivatives. Quinoxalines have received a significant amount of attention due to their potential use in fighting various pathophysiological conditions like epilepsy, Parkinson閳ユ獨, and Alzheimer閳ユ獨 diseases. Quinoxaline-1,4-di-N-oxide derivatives have shown to improve the biological results and are endowed with anti-viral, anti-cancer, anti-bacterial, and anti-protozoal activities with application in many other therapeutic areas.Application of 1910-90-3
Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider