Facile synthesis of 3,4-fused tricyclic indoles with a seven-membered ring through a three-component reaction of 4-hydroxyindole, aldehyde, and malonodinitrile or ethyl cyanoacetate

Bai, Ruke; Yang, Jian; Min, Lijun; Liu, Changhui; Wu, Fengtian; Gu, Yanlong

doi:10.1016/j.tet.2016.03.014

Cited by 7 publications

(2 citation statements)

References 47 publications

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“…[159] In 2016, Gu et al first described an elegant three-component reaction of arylformylacetonitriles 1 with aldehydes 129 and 4-hydroxyindole 130 in the presence of KF as catalyst, which delivered a 3,4-fused tricyclic indole 131 exhibiting a seven-membered ring in 61 % yield (Scheme 22). [160] This strategy utilized commercially available substrates and inspired synthetic chemists to use easily available indoles in many other reactions, which can be used to synthesize other valuable indole-containing compounds.…”

Section: Fused O-heterocyclesmentioning

confidence: 99%

Arylformylacetonitriles in Multicomponent Reactions Leading to Heterocycles

Yuan

2022

Eur J Org Chem

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Arylformylacetonitriles are versatile and attractive synthons in organic synthesis owing to their high reactivity. Among the numerous transformations involving arylformylacetonitriles, multicomponent reactions (MCRs) offer straightforward and effective routes to assemble the reactants into a wide range of five-and six-membered heterocyclic systems including pyrrole, pyrazole, triazole, furan, pyridine, pyrimidine, and pyran. This review collects the recent advances and applications of arylformylacetonitriles in MCRs for the synthesis of monocyclic or polycyclic heterocycles published in the literature since 2001.

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Section: Fused O-heterocyclesmentioning

confidence: 99%

Arylformylacetonitriles in Multicomponent Reactions Leading to Heterocycles

Yuan

2022

Eur J Org Chem

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“…2 Representative examples are shown in Fig. 1, including aurantioclavine, 3 clavicipitic acid, 4 communesin F, 5 and dragmacidin E. 6 Although great endeavors have been made to construct these 3,4-fused tricyclic indoles using functionalized indole derivatives as starting materials 7 or indole ring formation strategies, 8 the development of an efficient method to construct chiral 7-membered-ring-bridged 3,4-fused tricyclic indole frameworks is highly desirable.…”

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confidence: 99%