Acid-Catalyzed Multicomponent Tandem Cyclizations: Access to Polyfunctional Dihydroindolizino[8,7-<i>b</i>]indoles

Cai, Qun; Li, Deng‐Kui; Zhou, Ruoyu; Shu, Wen‐Ming; Wu, Yan‐Dong; Wu, An‐Xin

doi:10.1021/acs.orglett.6b00281

Cited by 43 publications

(30 citation statements)

References 45 publications

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“…In 2016, Cai et al. developed a one‐pot methodology, comprising tandem Pictet‐Spengler condensation followed by post‐intramolecular cyclization for the synthesis of highly functionalized dihydroindolozine[8,7‐ a ]indole scaffold (Scheme ) . The synthesis of two types of highly substituted dihydro‐β‐carboline fused pyrrole analogues 84 and 87 were reported using tryptamine 82 , arylglyoxal monohydrate 83 and malononitrile or trans‐β‐nitro styrenes 86 .…”

Section: β‐Carboline Fused Heterocycles Synthesized Via Post‐pictet‐smentioning

confidence: 99%

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Singh

Kumar

Patil³

et al. 2020

Adv Synth Catal

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Pictet-Spengler reaction is a typical condensation reaction of β-arylethylamine or Tryptamine with an aldehyde or ketone followed by ring closure to generate tetrahydroisoquinoline (THIQ) and Tetrahydro-β-carboline (THβC), respectively. Both these key skeletons represent huge range of structurally diverse naturally occurring isoquinoline and indole alkaloids. Nature has synthesized structurally complex Reserpine, Ajmalicine as well as other related alkaloids using various biosynthetic pathways via Pictet-Spengler reaction followed by post-Pictet-Spengler cyclization (PPSC) stratergy. This biosynthetic process is the short and reliable method to access diverse range of polycyclic heterocycles. Over the period of last sixty years, several researchers have synthesized complex alkaloids without highlighting the synthetic utility of the post-Pictet-Spengler cyclization strategy. We summarized the synthesis of numerous natural products and related natural product inspired heterocyclic scaffolds which follow the PPSC strategy to demonstrate its usefulness for the construction of diverse compound collection.

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Section: β‐Carboline Fused Heterocycles Synthesized Via Post‐pictet‐smentioning

confidence: 99%

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Singh

Kumar

Patil³

et al. 2020

Adv Synth Catal

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“…Cai et al. developed a CF 3 SO 3 H‐catalyzed multicomponent tandem cyclization reaction of phenylglyoxal, β‐nitrostyrene, and tryptamine, which produced multifunctional dihydroindolizino[8,7 ‐b ]indoles 6 in good yield . In this cyclization reaction, the high reactivity of the phenylglyoxal component played a key role to enable three‐molecule assembly to occur under mild and metal‐free conditions (Scheme ).…”

Section: Aliphatic Axb3 Smentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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“…Due to the significant advancements made to develop step‐economic strategies toward fused heterocyclic frameworks, especially those containing privileged moieties, alternative, rapid, and versatile approaches to assemble fused pyrrole ring are still needed …”

Section: Introductionmentioning

confidence: 99%

“…An‐Xin Wu and co‐worker developed two strategies for the synthesis of pyrrole ring by Knoevenagel condensation and oxidative aromatization reaction. (Scheme a) . In addition, the Yan and co‐workers reported a three step procedure for the formation of fused pyrrole rings via in situ generation of β ‐enamino ester from the reaction between propargyl esters and tryptamine (Scheme b) .…”

Section: Introductionmentioning

confidence: 99%

Acid‐Catalyzed Four‐Component Tandem Double Cyclization: Access to Dihydroindolizino[8,7‐b]indoles

2019

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The novel one pot four‐component reaction for the construction of dihydroindolizino[8,7‐b]indoles and their derivatives have been developed from ninhydrine, tryptamine, dimetylene acetylene dicarboxylate and aliphatic alcohol. This reaction produces to go through via Pictet‐Spengler cyclization reaction and construction of C−C and C−N bond readily achieved under transition metal free condition. Meanwhile, advantageous of tandem double cyclization are not only reducing reaction steps but also waste production.

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Acid-Catalyzed Multicomponent Tandem Cyclizations: Access to Polyfunctional Dihydroindolizino[8,7-b]indoles

Cited by 43 publications

References 45 publications

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Post‐Pictet‐Spengler Cyclization (PPSC): A Strategy to Synthesize Polycyclic β‐Carboline‐Derived Natural Products and Biologically Active N‐Heterocycles

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Acid‐Catalyzed Four‐Component Tandem Double Cyclization: Access to Dihydroindolizino[8,7‐b]indoles

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