, volume 68 , issue 5 , pages 1552-1559

Facile synthesis of sulfenyl-substituted isocoumarins, heterocycle-fused pyrones and 3-(inden-1-ylidene)isobenzofuranones by FeCl3-promoted regioselective annulation of o-(1-alkynyl)benzoates and o-(1-alkynyl)heterocyclic carboxylates with disulfides

Qianqian Li ¹

Jianquan Hong ¹

Linhong Weng ¹

Xigeng Zhou ²

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Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, HanDan Road 220, Shanghai 200433, People’s Republic of China |

Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Handan Road 220, Shanghai 200433, People's Republic of China |

Publication type: Journal Article

Publication date: 2012-02-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2011.12.003

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Abstract

Reported herein is the FeCl3-promoted intermolecular sulfoesterification of o-(1-alkynyl)benzoates with disulfides, which provides a convenient and efficient method for synthesis of 4-sulfenylisocoumarins. Various functional groups such as methoxy, halides, ester, cyano and silicon groups in the substrates are tolerated, and heterocycle-fused chalcogenylpyrones are also successfully achieved directly from the corresponding heterocyclic precursors under the same reaction conditions. In addition, starting from diynylbenzoate, this reaction sequence can be combined with a bicyclization step leading to the tetracyclic (E)-3-(2-phenyl-3-phenylchalcogenylinden-1-ylidene)isobenzofuranone frameworks with high regiospecificity and exclusive trans stereoselectivity.

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Li Q. et al. Facile synthesis of sulfenyl-substituted isocoumarins, heterocycle-fused pyrones and 3-(inden-1-ylidene)isobenzofuranones by FeCl3-promoted regioselective annulation of o-(1-alkynyl)benzoates and o-(1-alkynyl)heterocyclic carboxylates with disulfides // Tetrahedron. 2012. Vol. 68. No. 5. pp. 1552-1559.

GOST all authors (up to 50) Copy

Li Q., Hong J., Weng L., Zhou X. Facile synthesis of sulfenyl-substituted isocoumarins, heterocycle-fused pyrones and 3-(inden-1-ylidene)isobenzofuranones by FeCl3-promoted regioselective annulation of o-(1-alkynyl)benzoates and o-(1-alkynyl)heterocyclic carboxylates with disulfides // Tetrahedron. 2012. Vol. 68. No. 5. pp. 1552-1559.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2011.12.003

UR - https://doi.org/10.1016/j.tet.2011.12.003

TI - Facile synthesis of sulfenyl-substituted isocoumarins, heterocycle-fused pyrones and 3-(inden-1-ylidene)isobenzofuranones by FeCl3-promoted regioselective annulation of o-(1-alkynyl)benzoates and o-(1-alkynyl)heterocyclic carboxylates with disulfides

T2 - Tetrahedron

AU - Li, Qianqian

AU - Hong, Jianquan

AU - Weng, Linhong

AU - Zhou, Xigeng

PY - 2012

DA - 2012/02/01

PB - Elsevier

SP - 1552-1559

IS - 5

VL - 68

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2012_Li,

author = {Qianqian Li and Jianquan Hong and Linhong Weng and Xigeng Zhou},

title = {Facile synthesis of sulfenyl-substituted isocoumarins, heterocycle-fused pyrones and 3-(inden-1-ylidene)isobenzofuranones by FeCl3-promoted regioselective annulation of o-(1-alkynyl)benzoates and o-(1-alkynyl)heterocyclic carboxylates with disulfides},

journal = {Tetrahedron},

year = {2012},

volume = {68},

publisher = {Elsevier},

month = {feb},

url = {https://doi.org/10.1016/j.tet.2011.12.003},

number = {5},

pages = {1552--1559},

doi = {10.1016/j.tet.2011.12.003}

}

MLA

Cite this

MLA Copy

Li, Qianqian, et al. “Facile synthesis of sulfenyl-substituted isocoumarins, heterocycle-fused pyrones and 3-(inden-1-ylidene)isobenzofuranones by FeCl3-promoted regioselective annulation of o-(1-alkynyl)benzoates and o-(1-alkynyl)heterocyclic carboxylates with disulfides.” Tetrahedron, vol. 68, no. 5, Feb. 2012, pp. 1552-1559. https://doi.org/10.1016/j.tet.2011.12.003.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)