Phosphine-Mediated [4 + 3] Annulation of Diynoates and 2-Arylidene Indane-1,3-diones: Access of Indeno[1,2- b]oxepin-4-ylidenes and beyond

Sureshbabu Nallapati; Min Feng Tseng; Pei Ling Chen; Shih Ching Chuang

doi:10.1021/acs.orglett.2c00893

Phosphine-Mediated [4 + 3] Annulation of Diynoates and 2-Arylidene Indane-1,3-diones: Access of Indeno[1,2- b]oxepin-4-ylidenes and beyond

Sureshbabu Nallapati, Min Feng Tseng, Pei Ling Chen, Shih Ching Chuang^*

^*Corresponding author for this work

Department of Applied Chemistry

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

8 Scopus citations

Abstract

A novel unprecedented triphenylphosphine-mediated [4 + 3] annulation reaction of 2-benzylidene indane-1,3-diones and -diynoates through initial phosphine α-addition was discovered and found to result in biologically interesting indeno[1,2-b]oxepin-4-ylidenes in up to 75% yield. The seven-membered separable Z and E isomeric oxepins were confirmed using single-crystal X-ray diffraction.

Original language	English
Pages (from-to)	2993-2997
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.2c00893
State	Published - 29 Apr 2022

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title = "Phosphine-Mediated [4 + 3] Annulation of Diynoates and 2-Arylidene Indane-1,3-diones: Access of Indeno[1,2- b]oxepin-4-ylidenes and beyond",

abstract = "A novel unprecedented triphenylphosphine-mediated [4 + 3] annulation reaction of 2-benzylidene indane-1,3-diones and -diynoates through initial phosphine α-addition was discovered and found to result in biologically interesting indeno[1,2-b]oxepin-4-ylidenes in up to 75% yield. The seven-membered separable Z and E isomeric oxepins were confirmed using single-crystal X-ray diffraction.",

author = "Sureshbabu Nallapati and Tseng, {Min Feng} and Chen, {Pei Ling} and Chuang, {Shih Ching}",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

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day = "29",

doi = "10.1021/acs.orglett.2c00893",

language = "English",

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T1 - Phosphine-Mediated [4 + 3] Annulation of Diynoates and 2-Arylidene Indane-1,3-diones

T2 - Access of Indeno[1,2- b]oxepin-4-ylidenes and beyond

AU - Nallapati, Sureshbabu

AU - Tseng, Min Feng

AU - Chen, Pei Ling

AU - Chuang, Shih Ching

PY - 2022/4/29

Y1 - 2022/4/29

N2 - A novel unprecedented triphenylphosphine-mediated [4 + 3] annulation reaction of 2-benzylidene indane-1,3-diones and -diynoates through initial phosphine α-addition was discovered and found to result in biologically interesting indeno[1,2-b]oxepin-4-ylidenes in up to 75% yield. The seven-membered separable Z and E isomeric oxepins were confirmed using single-crystal X-ray diffraction.

AB - A novel unprecedented triphenylphosphine-mediated [4 + 3] annulation reaction of 2-benzylidene indane-1,3-diones and -diynoates through initial phosphine α-addition was discovered and found to result in biologically interesting indeno[1,2-b]oxepin-4-ylidenes in up to 75% yield. The seven-membered separable Z and E isomeric oxepins were confirmed using single-crystal X-ray diffraction.

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U2 - 10.1021/acs.orglett.2c00893

DO - 10.1021/acs.orglett.2c00893

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SN - 1523-7060

VL - 24

SP - 2993

EP - 2997

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

Phosphine-Mediated [4 + 3] Annulation of Diynoates and 2-Arylidene Indane-1,3-diones: Access of Indeno[1,2- b]oxepin-4-ylidenes and beyond

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