ChemInform Abstract: Regiochemical Studies of the Ring Expansion Reactions of Hydroxy Azides with Cyclic Ketones.

Brenton T. Smith; Vijaya Gracias; Jeffrey Aube

doi:10.1002/chin.200043177

ChemInform Abstract: Regiochemical Studies of the Ring Expansion Reactions of Hydroxy Azides with Cyclic Ketones.

ChemInform ◽

10.1002/chin.200043177 ◽

2000 ◽

Vol 31 (43) ◽

pp. no-no

Author(s):

Brenton T. Smith ◽

Vijaya Gracias ◽

Jeffrey Aube

Keyword(s):

Ring Expansion ◽

Cyclic Ketones ◽

Hydroxy Azides

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Ring Expansion of Cyclic Ketones by Reaction with β- and γ-Hydroxy Azides

Category 3, Compounds with Four and Three Carbon Heteroatom Bonds ◽

10.1055/sos-sd-022-00331 ◽

2005 ◽

pp. 1

Author(s):

S. Cicchi ◽

F. M. Cordero

Keyword(s):

Ring Expansion ◽

Cyclic Ketones ◽

Hydroxy Azides

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Regiochemical Studies of the Ring Expansion Reactions of Hydroxy Azides with Cyclic Ketones

The Journal of Organic Chemistry ◽

10.1021/jo000056b ◽

2000 ◽

Vol 65 (12) ◽

pp. 3771-3774 ◽

Cited By ~ 47

Author(s):

Brenton T. Smith ◽

Vijaya Gracias ◽

Jeffrey Aubé

Keyword(s):

Ring Expansion ◽

Cyclic Ketones ◽

Hydroxy Azides

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Study of the transamidative ring expansion of N-ω-halogenoalkyl-β-lactams of alkyl chain lengths 2–12 in liquid ammonia and other liquid amines: syntheses of 7-, 8- and 9-membered 1,5-diaza cyclic ketones, including routes to (±)-dihydroperiphylline and (±)-celabenzine

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19930002027 ◽

1993 ◽

pp. 2027-2046 ◽

Cited By ~ 19

Author(s):

Michael J. Begley ◽

Leslie Crombie ◽

David Haigh ◽

Raymond C. F. Jones ◽

Steven Osborne ◽

...

Keyword(s):

Liquid Ammonia ◽

Alkyl Chain ◽

Ring Expansion ◽

Cyclic Ketones ◽

Chain Lengths

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ChemInform Abstract: Carbenoid-Type Base-Induced Ring Expansion of the Adducts of Cyclic Ketones with Bis(phenylthio)methyllithium.

ChemInform ◽

10.1002/chin.198745133 ◽

1987 ◽

Vol 18 (45) ◽

Author(s):

W. D. ABRAHAM ◽

M. BHUPATHY ◽

T. COHEN

Keyword(s):

Ring Expansion ◽

Cyclic Ketones

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Migratory selectivity in the ring expansion of .alpha.,.beta.-unsaturated cyclic ketones via .beta.-hydroxy selenides

The Journal of Organic Chemistry ◽

10.1021/jo00225a043 ◽

1985 ◽

Vol 50 (25) ◽

pp. 5200-5204 ◽

Cited By ~ 15

Author(s):

Leo A. Paquette ◽

John R. Peterson ◽

Robert J. Ross

Keyword(s):

Ring Expansion ◽

Cyclic Ketones ◽

Alpha Beta

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ChemInform Abstract: Ring Expansion by in situ Tethering of Hydroxy Azides to Ketones: The Boyer Reaction.

ChemInform ◽

10.1002/chin.199811185 ◽

2010 ◽

Vol 29 (11) ◽

pp. no-no

Author(s):

V. GRACIAS ◽

K. E. FRANK ◽

G. L. MILLIGAN ◽

J. AUBE

Keyword(s):

Ring Expansion ◽

Hydroxy Azides

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α-Diazoacetamides in Sc(OTf)3-Catalyzed Tiffeneau–Demjanov Ring Expansion: Application towards the Synthesis of Rare Bicyclic Pyrazoles

Synlett ◽

10.1055/s-0039-1690047 ◽

2020 ◽

Vol 31 (04) ◽

pp. 373-377

Author(s):

Mikhail Krasavin ◽

Sergey Chuprun ◽

Dmitry Dar’in ◽

Grigory Kantin ◽

Petr Zhmurov

Keyword(s):

Ring Expansion ◽

Cyclic Ketones ◽

Lawesson’S Reagent ◽

Lawesson's Reagent

A novel Sc(OTf)3-catalyzed Tiffeneau–Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson’s reagent.

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