Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides

Lucjan Strekowski; Steven Patterson; Marek T. Cegla; Roman L. Wydra; Agnieszka Czarny; Donald B. Harden

doi:10.1016/S0040-4039(01)93740-2

Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides

Lucjan Strekowski, Steven Patterson, Marek T. Cegla, Roman L. Wydra, Agnieszka Czarny, Donald B. Harden

Center for Drug Design

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

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Abstract

Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.

Original language	English (US)
Pages (from-to)	5197-5200
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4039(01)93740-2
State	Published - 1989

Bibliographical note

Funding Information:
ACKNOWLEDGMENTS are made to the PetroleumR esearchF und, administeredb y the American Chemical Society, and NIH (Grants # AI27196 and S07-RR07171) for support of this research. The Varian VXR-400 NMR spectrometerw as obtained with partial support from an award by the NSF Chemical InstrumentationP rogram (CHEM-8409599).

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title = "Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides",

abstract = "Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.",

author = "Lucjan Strekowski and Steven Patterson and Cegla, {Marek T.} and Wydra, {Roman L.} and Agnieszka Czarny and Harden, {Donald B.}",

note = "Funding Information: ACKNOWLEDGMENTS are made to the PetroleumR esearchF und, administeredb y the American Chemical Society, and NIH (Grants # AI27196 and S07-RR07171) for support of this research. The Varian VXR-400 NMR spectrometerw as obtained with partial support from an award by the NSF Chemical InstrumentationP rogram (CHEM-8409599).",

year = "1989",

doi = "10.1016/S0040-4039(01)93740-2",

language = "English (US)",

volume = "30",

pages = "5197--5200",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "39",

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TY - JOUR

T1 - Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides

AU - Strekowski, Lucjan

AU - Patterson, Steven

AU - Cegla, Marek T.

AU - Wydra, Roman L.

AU - Czarny, Agnieszka

AU - Harden, Donald B.

N1 - Funding Information: ACKNOWLEDGMENTS are made to the PetroleumR esearchF und, administeredb y the American Chemical Society, and NIH (Grants # AI27196 and S07-RR07171) for support of this research. The Varian VXR-400 NMR spectrometerw as obtained with partial support from an award by the NSF Chemical InstrumentationP rogram (CHEM-8409599).

PY - 1989

Y1 - 1989

N2 - Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.

AB - Lithium diisopropylamide undergoes an addition reaction to the methyleneamino moiety of the title Schiff's bases substituted with a cyano group at the ortho or para position of the aniline, but mediates tautomerization of the unsubstituted and meta-substituted derivatives into secondary enamines. Only the tautomerization is observed for lithium 2,2,6,6-tetramethylpiperidide-mediated reactions.

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U2 - 10.1016/S0040-4039(01)93740-2

DO - 10.1016/S0040-4039(01)93740-2

M3 - Article

AN - SCOPUS:33747811923

SN - 0040-4039

VL - 30

SP - 5197

EP - 5200

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

Addition and lithiation reactions of N-(1-phenylalkylidene)anilines with lithium dialkylamides

Abstract

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