Cyclization of lithiated pyridine and quinoline carboxamides: Synthesis of partially saturated pyrrolopyridines and spirocyclic β-lactams

Jonathan Clayden; Stuart D. Hamilton; Rukhsana T. Mohammed

doi:10.1021/ol051214u

Cyclization of lithiated pyridine and quinoline carboxamides: Synthesis of partially saturated pyrrolopyridines and spirocyclic β-lactams

Jonathan Clayden, Stuart D. Hamilton, Rukhsana T. Mohammed

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

Abstract

(Chemical Equation Presented) Lithiation of N-benzyl pyridine and quinoline carboxamides α to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring- containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic β-lactams. © 2005 American Chemical Society.

Original language	English
Pages (from-to)	3673-3676
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	17
DOIs	https://doi.org/10.1021/ol051214u
Publication status	Published - 18 Aug 2005

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10.1021/ol051214u

CCDC 289323: Experimental Crystal Structure Determination
Clayden, J. (Contributor), Hamilton, S. D. (Contributor) & Mohammed, R. T. (Contributor), Cambridge Crystallographic Data Centre, 2005
DOI: 10.5517/cc9q202, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc9q202&sid=DataCite
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@article{b8820a8e0e5c4f36afda0fa6c273b30e,

title = "Cyclization of lithiated pyridine and quinoline carboxamides: Synthesis of partially saturated pyrrolopyridines and spirocyclic β-lactams",

abstract = "(Chemical Equation Presented) Lithiation of N-benzyl pyridine and quinoline carboxamides α to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring- containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic β-lactams. {\textcopyright} 2005 American Chemical Society.",

author = "Jonathan Clayden and Hamilton, {Stuart D.} and Mohammed, {Rukhsana T.}",

year = "2005",

month = aug,

day = "18",

doi = "10.1021/ol051214u",

language = "English",

volume = "7",

pages = "3673--3676",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Cyclization of lithiated pyridine and quinoline carboxamides: Synthesis of partially saturated pyrrolopyridines and spirocyclic β-lactams

AU - Clayden, Jonathan

AU - Hamilton, Stuart D.

AU - Mohammed, Rukhsana T.

PY - 2005/8/18

Y1 - 2005/8/18

N2 - (Chemical Equation Presented) Lithiation of N-benzyl pyridine and quinoline carboxamides α to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring- containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic β-lactams. © 2005 American Chemical Society.

AB - (Chemical Equation Presented) Lithiation of N-benzyl pyridine and quinoline carboxamides α to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring- containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic β-lactams. © 2005 American Chemical Society.

U2 - 10.1021/ol051214u

DO - 10.1021/ol051214u

M3 - Article

VL - 7

SP - 3673

EP - 3676

JO - Organic Letters

JF - Organic Letters

SN - 1523-7052

IS - 17

ER -

Cyclization of lithiated pyridine and quinoline carboxamides: Synthesis of partially saturated pyrrolopyridines and spirocyclic β-lactams

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CCDC 289323: Experimental Crystal Structure Determination

Cite this