Selective Synthesis of Polyfunctionalized Pyrido[2,3-<i>b</i>]indoles by Multicomponent Domino Reactions

Hu, Jundie; Cao, Cheng‐Pao; Lin, Wei; Hu, Minghua; Huang, Zhibin; Shi, Daqing

doi:10.1021/jo501049m

Cited by 37 publications

(8 citation statements)

References 60 publications

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“…A base-catalyzed multicomponent synthesis, with high regiocontrol, was performed using a three- or four-component version, depending on the selected catalyst [ 190 ]. The catalyzed reaction allowed for the access of polyfunctionalized pyrido[2,3- b ]indoles ( Scheme 14 ).…”

Section: Catalysis In Stereoselective Mcrsmentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

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Section: Catalysis In Stereoselective Mcrsmentioning

confidence: 99%

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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“…A wide range of practical syntheses of pyridine derivatives using MW-irradiation have been reported in the last decade [30][31][32][33][34]. In a recent work, Hu et al [30] synthesized a series of novel polyfunctionalized pyrido [2,3-b]indoles.…”

Section: Pyridines Dihydropyridines Piperidinesmentioning

confidence: 99%

“…In a recent work, Hu et al [30] synthesized a series of novel polyfunctionalized pyrido [2,3-b]indoles. This unusual tricyclic scaffold is found in some natural compounds such as grossularine-1 (1) and -2 (2), mescengricin (3) and a GABA modulator 4 having antianxiolitic properties ( Figure 2).…”

Section: Pyridines Dihydropyridines Piperidinesmentioning

confidence: 99%

“…Among the 1,4-dihydropyridine derivatives, nifedipine (28), amlodipine (29) and nimodipine (30) [38,39] (Scheme 6) are potent calcium channel antagonists, used clinically for the treatment of cardiovascular diseases such as hypertension and angina pectoris [40]. In addition, others 1,4-dihydropyridines have been discovered as potent calcium channel agonists (such as BAY K 8644 (31)) [41,42].…”

Section: Pyridines Dihydropyridines Piperidinesmentioning

confidence: 99%

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Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

et al. 2016

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This review describes the formation of six-membered heterocyclic compounds and their fused analogues under microwave activation using modern organic transformations including cyclocondensation, cycloaddition, multicomponents and other modular reactions. The review is divided according to the main heterocycle types in order of increasing complexity, starting with heterocyclic systems containing one, two and three heteroatoms and their fused analogues. Recent microwave applications are reviewed, with special focus on the chemistry of bioactive compounds. Selected examples from the 2006 to 2015 literature are discussed.

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“…Domino (cascade) reactions are promising and powerful tools in organic and medical chemistry because of their high atom economy, highly complex and diverse products, efficiency in forming multiple bonds, and environmental friendliness [ 22 ]. Consequently, domino reactions have often been used for the construction of complex heterocycles [ 23 , 24 , 25 , 26 , 27 , 28 ]. As part of our program to develop new methods for the construction of important heterocycles by domino reactions [ 29 , 30 , 31 , 32 ], we report herein an efficient synthesis of acenaphtho[1,2- b ]indole derivatives via a domino reaction using l -proline as the catalyst.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Acenaphtho[1,2-b]indole Derivatives via Domino Reaction

et al. 2018

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Selective Synthesis of Polyfunctionalized Pyrido[2,3-b]indoles by Multicomponent Domino Reactions

Cited by 37 publications

References 60 publications

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

An Efficient Synthesis of Acenaphtho[1,2-b]indole Derivatives via Domino Reaction

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