Phosphine-mediated MBH-Type/Acyl transfer/wittig sequence for construction of functionalized furo[3,2-c]coumarins

Sandip Sambhaji Vagh; Bo Jhih Hou; Athukuri Edukondalu; Pin Ching Wang; Wenwei Lin

doi:10.1021/acs.orglett.0c04082

Phosphine-mediated MBH-Type/Acyl transfer/wittig sequence for construction of functionalized furo[3,2-c]coumarins

Sandip Sambhaji Vagh, Bo Jhih Hou, Athukuri Edukondalu, Pin Ching Wang, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

25 Citations (Scopus)

Abstract

A new method for the construction of functionalized furo[3,2-c]coumarins via MBH-type/acyl-transfer/Wittig reaction is reported. The current approach would open a new route for the simultaneous formation of two rings in a one-pot reaction which is accompanied by incorporation of a keto functionality on the furan ring by activating the terminal alkynoates with phosphine. Furthermore, this protocol could also be applicable to the internal alkynoates/propiolamides to generate the 2,3-disubstituted furo[3,2-c]coumarins/furo[3,2-c]quinolinones by excluding the acyl-transfer reaction.

Original language	English
Pages (from-to)	842-846
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.0c04082
Publication status	Published - 2021 Feb 5

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c04082

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title = "Phosphine-mediated MBH-Type/Acyl transfer/wittig sequence for construction of functionalized furo[3,2-c]coumarins",

abstract = "A new method for the construction of functionalized furo[3,2-c]coumarins via MBH-type/acyl-transfer/Wittig reaction is reported. The current approach would open a new route for the simultaneous formation of two rings in a one-pot reaction which is accompanied by incorporation of a keto functionality on the furan ring by activating the terminal alkynoates with phosphine. Furthermore, this protocol could also be applicable to the internal alkynoates/propiolamides to generate the 2,3-disubstituted furo[3,2-c]coumarins/furo[3,2-c]quinolinones by excluding the acyl-transfer reaction.",

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doi = "10.1021/acs.orglett.0c04082",

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T1 - Phosphine-mediated MBH-Type/Acyl transfer/wittig sequence for construction of functionalized furo[3,2-c]coumarins

AU - Vagh, Sandip Sambhaji

AU - Hou, Bo Jhih

AU - Edukondalu, Athukuri

AU - Wang, Pin Ching

AU - Lin, Wenwei

PY - 2021/2/5

Y1 - 2021/2/5

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AB - A new method for the construction of functionalized furo[3,2-c]coumarins via MBH-type/acyl-transfer/Wittig reaction is reported. The current approach would open a new route for the simultaneous formation of two rings in a one-pot reaction which is accompanied by incorporation of a keto functionality on the furan ring by activating the terminal alkynoates with phosphine. Furthermore, this protocol could also be applicable to the internal alkynoates/propiolamides to generate the 2,3-disubstituted furo[3,2-c]coumarins/furo[3,2-c]quinolinones by excluding the acyl-transfer reaction.

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Phosphine-mediated MBH-Type/Acyl transfer/wittig sequence for construction of functionalized furo[3,2-c]coumarins

Abstract

ASJC Scopus subject areas

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CCDC 2039765: Experimental Crystal Structure Determination

CCDC 2039766: Experimental Crystal Structure Determination

CCDC 2039605: Experimental Crystal Structure Determination

Cite this

Phosphine-mediated MBH-Type/Acyl transfer/wittig sequence for construction of functionalized furo[3,2-c]coumarins

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 2039765: Experimental Crystal Structure Determination

CCDC 2039766: Experimental Crystal Structure Determination

CCDC 2039605: Experimental Crystal Structure Determination

Cite this