In 2018,Yonekura, Kyohei; Shinoda, Mika; Yonekura, Yuko; Tsuchimoto, Teruhisa published 《Indium-catalyzed annulation of o-acylanilines with alkoxyheteroarenes: synthesis of heteroaryl[b]quinolines and subsequent transformation to cryptolepine derivatives》.Molecules published the findings.Category: bromides-buliding-blocks The information in the text is summarized as follows:
An efficient method for the synthesis of heteroaryl[b]quinolines such as I [R = H, 4-OH, 2,3-di-MeO, etc.; R1 = Me, i-Pr, Ph, etc.; X = N, S] was developed via annulation of o-acylanilines and MeO-heteroarenes using an indium Lewis acid as catalyst for tandem N-C and C-C bond formation. A series of indolo[3,2-b]quinolines was subsequently transformed to structurally unprecedented cryptolepine derivatives Mechanistic studies showed that the N-C bond formation was followed by the C-C bond formation. The indium-catalyzed annulation reaction thus started with the nucleophilic attack of the NH2 group of o-acylanilines to the MeO-connected carbon atom of the heteroaryl ring in an SNAr fashion and thereby the N-C bond was formed. The resulting intermediate then cyclized and gave C-C bond through the nucleophilic attack of the heteroaryl-ring-based carbon atom to the carbonyl carbon atom, provided the HA[b]Q after aromatizing dehydration. The experimental process involved the reaction of Indium(III) bromide(cas: 13465-09-3Category: bromides-buliding-blocks)
Indium(III) bromide(cas: 13465-09-3) is used as a catalyst to produce dithioacetals when unactivated alkynes react with thiols and fields such as optics and microelectronics that utilize semiconductor technology have wide uses for indium in high-performing solar cells.Category: bromides-buliding-blocks
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary