Facile and efficient one-pot synthesis of highly functionalized thieno[2,3-b]thiopyran-4-ones from β-keto ε-xanthyl phosphonates

Matthieu Corbet; Samir Z. Zard

doi:10.1021/ol801033e

Facile and efficient one-pot synthesis of highly functionalized thieno[2,3-b]thiopyran-4-ones from β-keto ε-xanthyl phosphonates

Matthieu Corbet
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

(Chemical Equation Presented) The one-pot synthesis of various functionalized thieno[2,3-b]thiopyran-4-ones from readily available β-keto ε-xanthyl phosphonates has been accomplished by combining a Horner - Wadsworth - Emmons olefination with a base-induced intramolecular domino cyclization/thio-Michael addition. The use of cyclic ketones in this transformation allowed a facile access to novel spiro-type thieno[2,3-b] thiopyran structures.

Original language	English
Pages (from-to)	2861-2864
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	13
DOIs	https://doi.org/10.1021/ol801033e
Publication status	Published - 1 Dec 2008
Externally published	Yes

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title = "Facile and efficient one-pot synthesis of highly functionalized thieno[2,3-b]thiopyran-4-ones from β-keto ε-xanthyl phosphonates",

abstract = "(Chemical Equation Presented) The one-pot synthesis of various functionalized thieno[2,3-b]thiopyran-4-ones from readily available β-keto ε-xanthyl phosphonates has been accomplished by combining a Horner - Wadsworth - Emmons olefination with a base-induced intramolecular domino cyclization/thio-Michael addition. The use of cyclic ketones in this transformation allowed a facile access to novel spiro-type thieno[2,3-b] thiopyran structures.",

author = "Matthieu Corbet and Zard, \{Samir Z.\}",

year = "2008",

month = dec,

day = "1",

doi = "10.1021/ol801033e",

language = "English",

volume = "10",

pages = "2861--2864",

journal = "Organic Letters",

issn = "1523-7060",

number = "13",

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T1 - Facile and efficient one-pot synthesis of highly functionalized thieno[2,3-b]thiopyran-4-ones from β-keto ε-xanthyl phosphonates

AU - Corbet, Matthieu

AU - Zard, Samir Z.

PY - 2008/12/1

Y1 - 2008/12/1

N2 - (Chemical Equation Presented) The one-pot synthesis of various functionalized thieno[2,3-b]thiopyran-4-ones from readily available β-keto ε-xanthyl phosphonates has been accomplished by combining a Horner - Wadsworth - Emmons olefination with a base-induced intramolecular domino cyclization/thio-Michael addition. The use of cyclic ketones in this transformation allowed a facile access to novel spiro-type thieno[2,3-b] thiopyran structures.

AB - (Chemical Equation Presented) The one-pot synthesis of various functionalized thieno[2,3-b]thiopyran-4-ones from readily available β-keto ε-xanthyl phosphonates has been accomplished by combining a Horner - Wadsworth - Emmons olefination with a base-induced intramolecular domino cyclization/thio-Michael addition. The use of cyclic ketones in this transformation allowed a facile access to novel spiro-type thieno[2,3-b] thiopyran structures.

U2 - 10.1021/ol801033e

DO - 10.1021/ol801033e

M3 - Article

AN - SCOPUS:58149303348

SN - 1523-7060

VL - 10

SP - 2861

EP - 2864

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Facile and efficient one-pot synthesis of highly functionalized thieno[2,3-b]thiopyran-4-ones from β-keto ε-xanthyl phosphonates

Abstract

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