A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines

Jill B. Williamson; Emily R. Smith; Jonathan R. Scheerer

doi:10.1055/s-0036-1588729

A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines

Jill B. Williamson
, Emily R. Smith
, Jonathan R. Scheerer

Chemistry

Stony Brook University

College of William and Mary

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

5 Scopus citations

Abstract

A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Diels-Alder, and retrograde Diels-Alder with loss of CO ₂ occurs in the same reaction vessel to provide polysubstituted tricyclic pyridine products.

Original language	English
Pages (from-to)	1170-1172
Number of pages	3
Journal	Synlett
Volume	28
Issue number	10
DOIs	https://doi.org/10.1055/s-0036-1588729
State	Published - Jun 19 2017

Keywords

Diels-Alder
cycloaddition
cycloreversion
domino reactions
oxazinone
pyridine synthesis

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10.1055/s-0036-1588729

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title = "A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines",

abstract = "A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Diels-Alder, and retrograde Diels-Alder with loss of CO 2 occurs in the same reaction vessel to provide polysubstituted tricyclic pyridine products.",

keywords = "Diels-Alder, cycloaddition, cycloreversion, domino reactions, oxazinone, pyridine synthesis",

author = "Williamson, \{Jill B.\} and Smith, \{Emily R.\} and Scheerer, \{Jonathan R.\}",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart, New York.",

year = "2017",

month = jun,

day = "19",

doi = "10.1055/s-0036-1588729",

language = "English",

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journal = "Synlett",

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T1 - A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines

AU - Williamson, Jill B.

AU - Smith, Emily R.

AU - Scheerer, Jonathan R.

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart, New York.

PY - 2017/6/19

Y1 - 2017/6/19

N2 - A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Diels-Alder, and retrograde Diels-Alder with loss of CO 2 occurs in the same reaction vessel to provide polysubstituted tricyclic pyridine products.

AB - A domino reaction sequence has been evaluated that begins with union of novel dihydrooxazinone precursors with 2-alkynyl-substituted benzaldehyde components through aldol condensation. Ensuing operations, including alkene isomerization, Diels-Alder, and retrograde Diels-Alder with loss of CO 2 occurs in the same reaction vessel to provide polysubstituted tricyclic pyridine products.

KW - Diels-Alder

KW - cycloaddition

KW - cycloreversion

KW - domino reactions

KW - oxazinone

KW - pyridine synthesis

UR - https://www.scopus.com/pages/publications/85013817873

U2 - 10.1055/s-0036-1588729

DO - 10.1055/s-0036-1588729

M3 - Article

SN - 0936-5214

VL - 28

SP - 1170

EP - 1172

JO - Synlett

JF - Synlett

IS - 10

ER -

A Merged Aldol Condensation, Alkene Isomerization, Cycloaddition/Cycloreversion Sequence Employing Oxazinone Intermediates for the Synthesis of Substituted Pyridines

Abstract

Keywords

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