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

doi:10.1002/adsc.201400424

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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

14 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 language	English
Pages (from-to)	3849-3860
Number of pages	12
Journal	Advanced Synthesis and Catalysis
Volume	356
Issue number	18
DOIs	https://doi.org/10.1002/adsc.201400424
Publication status	Published - 2014 Dec 15

Keywords

Indolo-benzonaphthyridine
Indolylnitroalkene
Indolyltetrahydro quinoline
Iron(III) chloride

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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CCDC 993414: Experimental Crystal Structure Determination
Zanwar, M. R. (Creator), Gawande, S. D. (Creator), Kavala, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc12bqmr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12bqmr&sid=DataCite
Dataset
CCDC 993413: Experimental Crystal Structure Determination
Zanwar, M. R. (Creator), Gawande, S. D. (Creator), Kavala, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc12bqlq, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12bqlq&sid=DataCite
Dataset
CCDC 993412: Experimental Crystal Structure Determination
Zanwar, M. R. (Creator), Gawande, S. D. (Creator), Kavala, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc12bqkp, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12bqkp&sid=DataCite
Dataset

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Zanwar, M. R., Gawande, S. D., Kavala, V., Kuo, C. W., & Yao, C. F. (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, 356(18), 3849-3860. https://doi.org/10.1002/adsc.201400424

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

Research output: Contribution to journal › Article › peer-review

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, Manoj R. ; Gawande, Sachin D. ; Kavala, Veerababurao et al. / 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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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.",

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AU - Zanwar, Manoj R.

AU - Gawande, Sachin D.

AU - Kavala, Veerababurao

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

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KW - Indolyltetrahydro quinoline

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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

Abstract

Keywords

ASJC Scopus subject areas

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Datasets

CCDC 993414: Experimental Crystal Structure Determination

CCDC 993413: Experimental Crystal Structure Determination

CCDC 993412: Experimental Crystal Structure Determination

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