Iron(III) chloride catalyzed synthesis of highly substituted indolyl-tetrahydroquinoline derivatives by using indolylnitroalkene as dienophiles and its application to the synthesis of indolo-benzonaphthyridine derivatives

Manoj R. Zanwar, Sachin D. Gawande, Veerababurao Kavala, Chun Wei Kuo, Ching Fa Yao

Research output: Contribution to journal › Article

8 Citations (Scopus)

Abstract

An efficient iron(III) chloride catalyzed synthesis of highly substituted indolyltetrahydroquinoline derivatives from easily available starting materials, including indolylnitroalkenes, substituted anilines and various aldehydes is reported. The reaction utilized strong electron deficient dienophiles like indolylnitroalkene via a Povarov approach. The methodology shows good functional group tolerance and can be used to prepare fused indolo-benzonaphthyridine derivatives.

Original languageEnglish
Pages (from-to)3849-3860
Number of pages12
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number18
DOIs
Publication statusPublished - 2014 Dec 15

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Chlorides
Aniline Compounds
Iron
Derivatives
Aniline
Aldehydes
Functional groups
Electrons
1,2,3,4-tetrahydroquinoline

Keywords

  • Indolo-benzonaphthyridine
  • Indolylnitroalkene
  • Indolyltetrahydro quinoline
  • Iron(III) chloride

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Iron(III) chloride catalyzed synthesis of highly substituted indolyl-tetrahydroquinoline derivatives by using indolylnitroalkene as dienophiles and its application to the synthesis of indolo-benzonaphthyridine derivatives. / Zanwar, Manoj R.; Gawande, Sachin D.; Kavala, Veerababurao; Kuo, Chun Wei; Yao, Ching Fa.

In: Advanced Synthesis and Catalysis, Vol. 356, No. 18, 15.12.2014, p. 3849-3860.

Research output: Contribution to journal › Article

Zanwar, MR, Gawande, SD, Kavala, V, Kuo, CW & Yao, CF 2014, 'Iron(III) chloride catalyzed synthesis of highly substituted indolyl-tetrahydroquinoline derivatives by using indolylnitroalkene as dienophiles and its application to the synthesis of indolo-benzonaphthyridine derivatives', Advanced Synthesis and Catalysis, vol. 356, no. 18, pp. 3849-3860. https://doi.org/10.1002/adsc.201400424
Zanwar MR, Gawande SD, Kavala V, Kuo CW, Yao CF. Iron(III) chloride catalyzed synthesis of highly substituted indolyl-tetrahydroquinoline derivatives by using indolylnitroalkene as dienophiles and its application to the synthesis of indolo-benzonaphthyridine derivatives. Advanced Synthesis and Catalysis. 2014 Dec 15;356(18):3849-3860. https://doi.org/10.1002/adsc.201400424
Zanwar, Manoj R. ; Gawande, Sachin D. ; Kavala, Veerababurao ; Kuo, Chun Wei ; Yao, Ching Fa. / Iron(III) chloride catalyzed synthesis of highly substituted indolyl-tetrahydroquinoline derivatives by using indolylnitroalkene as dienophiles and its application to the synthesis of indolo-benzonaphthyridine derivatives. In: Advanced Synthesis and Catalysis. 2014 ; Vol. 356, No. 18. pp. 3849-3860.
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AU - Yao, Ching Fa

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