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A Stereoselective Povarov Reaction Leading to exo‐Tetrahydroindolo[3,2‐c]quinoline Derivatives Catalyzed by Iodine

We report an iodine‐catalyzed Povarov reaction using indole as dienophile carried out in toluene at room temperature. This three‐component reaction, coupling an aldehyde, an amine, and an indole, proved to be an efficient method for synthesizing ‐indolo[3,2‐]quinoline derivatives related to the alka... Full description

Journal Title: European Journal of Organic Chemistry September 2012, Vol.2012(25), pp.4811-4818
Main Author: Wang, Xiang‐Shan
Other Authors: Yin, Ming‐Yue , Wang, Wei , Tu, Shu‐Jiang
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1434-193X ; E-ISSN: 1099-0690 ; DOI: 10.1002/ejoc.201200551
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recordid: wj10.1002/ejoc.201200551
title: A Stereoselective Povarov Reaction Leading to exo‐Tetrahydroindolo[3,2‐c]quinoline Derivatives Catalyzed by Iodine
format: Article
creator:
  • Wang, Xiang‐Shan
  • Yin, Ming‐Yue
  • Wang, Wei
  • Tu, Shu‐Jiang
subjects:
  • Multicomponent Reactions
  • Homogeneous Catalysis
  • Iodine
  • Dia­stereoselectivity
  • Heterocycles
ispartof: European Journal of Organic Chemistry, September 2012, Vol.2012(25), pp.4811-4818
description: We report an iodine‐catalyzed Povarov reaction using indole as dienophile carried out in toluene at room temperature. This three‐component reaction, coupling an aldehyde, an amine, and an indole, proved to be an efficient method for synthesizing ‐indolo[3,2‐]quinoline derivatives related to the alkaloid isocryptolepine (cryptosanguinolentine) in good yield and with high stereoselectivity. ‐Indolo[3,2‐]quinoline derivatives related to the alkaloid isocryptolepine(cryptosanguinolentine) were synthesized by an iodine‐catalyzed Povarov reaction. This procedure has the advantages of good yield and high stereoselectivity.
language: eng
source:
identifier: ISSN: 1434-193X ; E-ISSN: 1099-0690 ; DOI: 10.1002/ejoc.201200551
fulltext: fulltext
issn:
  • 1434-193X
  • 1434193X
  • 1099-0690
  • 10990690
url: Link


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titleA Stereoselective Povarov Reaction Leading to exo‐Tetrahydroindolo[3,2‐c]quinoline Derivatives Catalyzed by Iodine
creatorWang, Xiang‐Shan ; Yin, Ming‐Yue ; Wang, Wei ; Tu, Shu‐Jiang
ispartofEuropean Journal of Organic Chemistry, September 2012, Vol.2012(25), pp.4811-4818
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subjectMulticomponent Reactions ; Homogeneous Catalysis ; Iodine ; Dia­stereoselectivity ; Heterocycles
descriptionWe report an iodine‐catalyzed Povarov reaction using indole as dienophile carried out in toluene at room temperature. This three‐component reaction, coupling an aldehyde, an amine, and an indole, proved to be an efficient method for synthesizing ‐indolo[3,2‐]quinoline derivatives related to the alkaloid isocryptolepine (cryptosanguinolentine) in good yield and with high stereoselectivity. ‐Indolo[3,2‐]quinoline derivatives related to the alkaloid isocryptolepine(cryptosanguinolentine) were synthesized by an iodine‐catalyzed Povarov reaction. This procedure has the advantages of good yield and high stereoselectivity.
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titleA Stereoselective Povarov Reaction Leading to exo‐Tetrahydroindolo[3,2‐c]quinoline Derivatives Catalyzed by Iodine
descriptionWe report an iodine‐catalyzed Povarov reaction using indole as dienophile carried out in toluene at room temperature. This three‐component reaction, coupling an aldehyde, an amine, and an indole, proved to be an efficient method for synthesizing ‐indolo[3,2‐]quinoline derivatives related to the alkaloid isocryptolepine (cryptosanguinolentine) in good yield and with high stereoselectivity. ‐Indolo[3,2‐]quinoline derivatives related to the alkaloid isocryptolepine(cryptosanguinolentine) were synthesized by an iodine‐catalyzed Povarov reaction. This procedure has the advantages of good yield and high stereoselectivity.
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titleA Stereoselective Povarov Reaction Leading to exo‐Tetrahydroindolo[3,2‐c]quinoline Derivatives Catalyzed by Iodine
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abstractWe report an iodine‐catalyzed Povarov reaction using indole as dienophile carried out in toluene at room temperature. This three‐component reaction, coupling an aldehyde, an amine, and an indole, proved to be an efficient method for synthesizing ‐indolo[3,2‐]quinoline derivatives related to the alkaloid isocryptolepine (cryptosanguinolentine) in good yield and with high stereoselectivity. ‐Indolo[3,2‐]quinoline derivatives related to the alkaloid isocryptolepine(cryptosanguinolentine) were synthesized by an iodine‐catalyzed Povarov reaction. This procedure has the advantages of good yield and high stereoselectivity.
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pubWILEY‐VCH Verlag
doi10.1002/ejoc.201200551
pages4811-4818
date2012-09