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

43 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

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Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Lin, W., Chen, L., & Knochel, P. (2007). Preparation of functionalized 3,4-pyridynes via 2-magnesiated diaryl sulfonates. Tetrahedron, 63(13), 2787-2797. https://doi.org/10.1016/j.tet.2007.01.027

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AU - Knochel, Paul

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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

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KW - Functionalized organomagnesium reagents

KW - Halogen-magnesium exchange

KW - Magnesium

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10.1016/j.tet.2007.01.027