Synthesis of indole derivatives via isocyanides

Abstract

Fast and convenient approaches to the indole nucleus from isocyanides are reviewed as a means for the tailored preparation of conveniently functionalized indoles by using the unique reactivity of isocyanides in one-pot multicomponent and cascade reactions.

Transition Metal‐Catalyzed Synthesis of Fused Five‐Membered Aromatic Heterocycles

“…Not surprisingly, investigation of the chemistry of this fascinating heterocycle has been sustained to be one of the most important objectives of heterocyclic chemistry for over 100 years. Great attention directed towards the synthesis of functionalized indole derivatives stimulated the establishment of a myriad of methods for their preparation [165][166][167][168][169][170][171][172][173][174][175][176][177]. Nonetheless, the development of novel general transition metal-catalyzed processes for the synthesis and functionalization of the indole ring system in a highly chemoand region-selective fashion continues to be of significant importance [148,163,167,176,[178][179][180][181].…”

Renaissance of Organic Synthesis Using Isocyanides

“…5 Among the various Nheterocycles that can be synthesized from isocyanides, indoles are particularly attractive targets in view of their widespread occurrence in natural and unnatural products. 40 In this context, Fukuyama disclosed that the reaction of 2-alkenylphenyl isocyanide with tin hydride under radical conditions affords 2-stannylindoles, which are amenable to further elaboration, for example, via the MigitaKosugiStille coupling (Scheme 9). 41 We felt that if this reaction could be extended to the synthesis of the corresponding boron analogs, it would lead to a nontoxic and more versatile platform for indole-based compounds on the basis of recent outstanding progress in organic synthesis using organoboron reagents.…”

Complementary regioselectivity in the synthesis of iminohydantoins: remarkable effect of amide substitution on the cyclization

“…2 Besides the characteristic chemistry of isocyanides with a formally divalent carbon, 3 two different approaches have been employed for the cyclization, the use of the active methylene 4 and the use of the amide group, either through the oxygen 5 or nitrogen atom.…”