Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates

Wenwei Lin; Ling Chen; Paul Knochel

doi:10.1016/j.tet.2007.01.027

Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates

Wenwei Lin, Ling Chen, Paul Knochel

Department of Chemistry

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

45 Citations (Scopus)

Abstract

The preparation of functionalized 3,4-pyridynes of type 1 as highly reactive intermediates has been achieved by the controlled elimination of readily generated 2-magnesiated diaryl sulfonates of type 2 obtained by a low temperature I/Mg- or Br/Mg-exchange starting from the corresponding halides of type 3. After trapping with furan, moderate to good yields of the desired functionalized cycloadducts of type 4 are obtained. The addition of a magnesium arylthiolate or magnesium phenylselenide to 3,4-pyridyne followed by quenching with an electrophile is also described.

Original language	English
Pages (from-to)	2787-2797
Number of pages	11
Journal	Tetrahedron
Volume	63
Issue number	13
DOIs	https://doi.org/10.1016/j.tet.2007.01.027
Publication status	Published - 2007 Mar 26

Keywords

Cycloaddition
Functionalized 3,4-pyridyne
Functionalized organomagnesium reagents
Halogen-magnesium exchange
Magnesium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates",

abstract = "The preparation of functionalized 3,4-pyridynes of type 1 as highly reactive intermediates has been achieved by the controlled elimination of readily generated 2-magnesiated diaryl sulfonates of type 2 obtained by a low temperature I/Mg- or Br/Mg-exchange starting from the corresponding halides of type 3. After trapping with furan, moderate to good yields of the desired functionalized cycloadducts of type 4 are obtained. The addition of a magnesium arylthiolate or magnesium phenylselenide to 3,4-pyridyne followed by quenching with an electrophile is also described.",

keywords = "Cycloaddition, Functionalized 3,4-pyridyne, Functionalized organomagnesium reagents, Halogen-magnesium exchange, Magnesium",

author = "Wenwei Lin and Ling Chen and Paul Knochel",

note = "Funding Information: We thank the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft (DFG) and Merck Research Laboratories (MSD) for financial support. We also thank Chemetall GmbH (Frankfurt) and BASF AG (Ludwigshafen) for the generous gift of chemicals. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

year = "2007",

month = mar,

day = "26",

doi = "10.1016/j.tet.2007.01.027",

language = "English",

volume = "63",

pages = "2787--2797",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

number = "13",

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TY - JOUR

T1 - Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates

AU - Lin, Wenwei

AU - Chen, Ling

AU - Knochel, Paul

N1 - Funding Information: We thank the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft (DFG) and Merck Research Laboratories (MSD) for financial support. We also thank Chemetall GmbH (Frankfurt) and BASF AG (Ludwigshafen) for the generous gift of chemicals. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2007/3/26

Y1 - 2007/3/26

N2 - The preparation of functionalized 3,4-pyridynes of type 1 as highly reactive intermediates has been achieved by the controlled elimination of readily generated 2-magnesiated diaryl sulfonates of type 2 obtained by a low temperature I/Mg- or Br/Mg-exchange starting from the corresponding halides of type 3. After trapping with furan, moderate to good yields of the desired functionalized cycloadducts of type 4 are obtained. The addition of a magnesium arylthiolate or magnesium phenylselenide to 3,4-pyridyne followed by quenching with an electrophile is also described.

AB - The preparation of functionalized 3,4-pyridynes of type 1 as highly reactive intermediates has been achieved by the controlled elimination of readily generated 2-magnesiated diaryl sulfonates of type 2 obtained by a low temperature I/Mg- or Br/Mg-exchange starting from the corresponding halides of type 3. After trapping with furan, moderate to good yields of the desired functionalized cycloadducts of type 4 are obtained. The addition of a magnesium arylthiolate or magnesium phenylselenide to 3,4-pyridyne followed by quenching with an electrophile is also described.

KW - Cycloaddition

KW - Functionalized 3,4-pyridyne

KW - Functionalized organomagnesium reagents

KW - Halogen-magnesium exchange

KW - Magnesium

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U2 - 10.1016/j.tet.2007.01.027

DO - 10.1016/j.tet.2007.01.027

M3 - Article

AN - SCOPUS:33847036007

VL - 63

SP - 2787

EP - 2797

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 13

ER -

Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates

Abstract

Keywords

ASJC Scopus subject areas

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