Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones

Himangsu Sekhar Dutta; Ashfaq Ahmad; Afsar Ali Khan; Mohit Kumar; null Raziullah; Jayanti Vaishnav; Manoj Kumar Gangwar; Ravi Sankar Ampapathi; Dipankar Koley

doi:10.1021/acs.joc.1c01872

Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones

Himangsu Sekhar Dutta, Ashfaq Ahmad, Afsar Ali Khan, Mohit Kumar, Raziullah, Jayanti Vaishnav, Manoj Kumar Gangwar, Ravi Sankar Ampapathi, Dipankar Koley

Catalysis Research Center

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

8 Scopus citations

Abstract

A ytterbium triflate-catalyzed diastereoselective [3 + 2] cycloaddition of quinoxalinones with donor–acceptor cyclopropanes and cyclobutanes is described. A series of tetrahydropyrrolo-quinoxalinone derivatives were obtained in high yields (up to 96%) with excellent diastereoselectivities (up to 46:1). Other medicinally important heterocycles like benzoxazinone, isoquinoxalinone, and dibenzoxazepine derivatives were also suitable for the desired annulation reaction. The current method is applicable for the scale-up reaction. Further, the utility of this annulation reaction is demonstrated by the synthesis of densely functionalized proline derivatives.

Original language	English (US)
Journal	The Journal of Organic Chemistry
DOIs	https://doi.org/10.1021/acs.joc.1c01872
State	Published - Nov 15 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-11-25
Acknowledgements: Financial support from DST-SERB (EMR/2016/000613), CSIR-New Delhi (H.S.D., A.A., A.A.K.), and UGC-New Delhi (M.K., R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. CDRI communication no 10313.

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.1c01872

Cite this

Dutta, H. S., Ahmad, A., Khan, A. A., Kumar, M., Raziullah, Vaishnav, J., Gangwar, M. K., Ampapathi, R. S., & Koley, D. (2021). Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones. The Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.1c01872

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title = "Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones",

abstract = "A ytterbium triflate-catalyzed diastereoselective [3 + 2] cycloaddition of quinoxalinones with donor–acceptor cyclopropanes and cyclobutanes is described. A series of tetrahydropyrrolo-quinoxalinone derivatives were obtained in high yields (up to 96%) with excellent diastereoselectivities (up to 46:1). Other medicinally important heterocycles like benzoxazinone, isoquinoxalinone, and dibenzoxazepine derivatives were also suitable for the desired annulation reaction. The current method is applicable for the scale-up reaction. Further, the utility of this annulation reaction is demonstrated by the synthesis of densely functionalized proline derivatives.",

author = "Dutta, {Himangsu Sekhar} and Ashfaq Ahmad and Khan, {Afsar Ali} and Mohit Kumar and Raziullah and Jayanti Vaishnav and Gangwar, {Manoj Kumar} and Ampapathi, {Ravi Sankar} and Dipankar Koley",

note = "KAUST Repository Item: Exported on 2021-11-25 Acknowledgements: Financial support from DST-SERB (EMR/2016/000613), CSIR-New Delhi (H.S.D., A.A., A.A.K.), and UGC-New Delhi (M.K., R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. CDRI communication no 10313.",

year = "2021",

month = nov,

day = "15",

doi = "10.1021/acs.joc.1c01872",

language = "English (US)",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones

AU - Dutta, Himangsu Sekhar

AU - Ahmad, Ashfaq

AU - Khan, Afsar Ali

AU - Kumar, Mohit

AU - Raziullah, null

AU - Vaishnav, Jayanti

AU - Gangwar, Manoj Kumar

AU - Ampapathi, Ravi Sankar

AU - Koley, Dipankar

N1 - KAUST Repository Item: Exported on 2021-11-25 Acknowledgements: Financial support from DST-SERB (EMR/2016/000613), CSIR-New Delhi (H.S.D., A.A., A.A.K.), and UGC-New Delhi (M.K., R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. CDRI communication no 10313.

PY - 2021/11/15

Y1 - 2021/11/15

N2 - A ytterbium triflate-catalyzed diastereoselective [3 + 2] cycloaddition of quinoxalinones with donor–acceptor cyclopropanes and cyclobutanes is described. A series of tetrahydropyrrolo-quinoxalinone derivatives were obtained in high yields (up to 96%) with excellent diastereoselectivities (up to 46:1). Other medicinally important heterocycles like benzoxazinone, isoquinoxalinone, and dibenzoxazepine derivatives were also suitable for the desired annulation reaction. The current method is applicable for the scale-up reaction. Further, the utility of this annulation reaction is demonstrated by the synthesis of densely functionalized proline derivatives.

AB - A ytterbium triflate-catalyzed diastereoselective [3 + 2] cycloaddition of quinoxalinones with donor–acceptor cyclopropanes and cyclobutanes is described. A series of tetrahydropyrrolo-quinoxalinone derivatives were obtained in high yields (up to 96%) with excellent diastereoselectivities (up to 46:1). Other medicinally important heterocycles like benzoxazinone, isoquinoxalinone, and dibenzoxazepine derivatives were also suitable for the desired annulation reaction. The current method is applicable for the scale-up reaction. Further, the utility of this annulation reaction is demonstrated by the synthesis of densely functionalized proline derivatives.

UR - http://hdl.handle.net/10754/673763

UR - https://pubs.acs.org/doi/10.1021/acs.joc.1c01872

U2 - 10.1021/acs.joc.1c01872

DO - 10.1021/acs.joc.1c01872

M3 - Article

C2 - 34780178

SN - 0022-3263

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

ER -

Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones

Abstract

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CCDC 2046700: Experimental Crystal Structure Determination : dimethyl 5-methyl-4-oxo-1-[4-(trifluoromethyl)phenyl]-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxaline-3,3(3aH)-dicarboxylate

CCDC 2046701: Experimental Crystal Structure Determination : dimethyl 10-(4-methoxyphenyl)-5-methyl-6-oxo-6,6a,9,10-tetrahydro-5H-pyrido[1,2-a]quinoxaline-7,7(8H)-dicarboxylate

Cite this

Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 2046700: Experimental Crystal Structure Determination : dimethyl 5-methyl-4-oxo-1-[4-(trifluoromethyl)phenyl]-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxaline-3,3(3aH)-dicarboxylate

CCDC 2046701: Experimental Crystal Structure Determination : dimethyl 10-(4-methoxyphenyl)-5-methyl-6-oxo-6,6a,9,10-tetrahydro-5H-pyrido[1,2-a]quinoxaline-7,7(8H)-dicarboxylate

Cite this