Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones

Eric Bacqué; Myriem El Qacemi; Samir Z. Zard

doi:10.1021/ol0489649

Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones

Eric Bacqué
, Myriem El Qacemi
, Samir Z. Zard

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

Abstract

(Chemical Equation Presented) Compounds containing a pyridine nucleus fused to a saturated nitrogen-containing ring, including 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones, were prepared in good yield starting from various 2,6-dichloropyridines. The method hinges on a free-radical xanthate-mediated cyclization or intermolecular addition/cyclization sequence for the construction of the new fused rings.

Original language	English
Pages (from-to)	3671-3674
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	21
DOIs	https://doi.org/10.1021/ol0489649
Publication status	Published - 14 Oct 2004
Externally published	Yes

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@article{04345ecc897b47d2a8b3eb4991bcadcf,

title = "Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones",

abstract = "(Chemical Equation Presented) Compounds containing a pyridine nucleus fused to a saturated nitrogen-containing ring, including 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones, were prepared in good yield starting from various 2,6-dichloropyridines. The method hinges on a free-radical xanthate-mediated cyclization or intermolecular addition/cyclization sequence for the construction of the new fused rings.",

author = "Eric Bacqu{\'e} and \{El Qacemi\}, Myriem and Zard, \{Samir Z.\}",

year = "2004",

month = oct,

day = "14",

doi = "10.1021/ol0489649",

language = "English",

volume = "6",

pages = "3671--3674",

journal = "Organic Letters",

issn = "1523-7060",

number = "21",

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TY - JOUR

T1 - Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones

AU - Bacqué, Eric

AU - El Qacemi, Myriem

AU - Zard, Samir Z.

PY - 2004/10/14

Y1 - 2004/10/14

N2 - (Chemical Equation Presented) Compounds containing a pyridine nucleus fused to a saturated nitrogen-containing ring, including 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones, were prepared in good yield starting from various 2,6-dichloropyridines. The method hinges on a free-radical xanthate-mediated cyclization or intermolecular addition/cyclization sequence for the construction of the new fused rings.

AB - (Chemical Equation Presented) Compounds containing a pyridine nucleus fused to a saturated nitrogen-containing ring, including 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones, were prepared in good yield starting from various 2,6-dichloropyridines. The method hinges on a free-radical xanthate-mediated cyclization or intermolecular addition/cyclization sequence for the construction of the new fused rings.

U2 - 10.1021/ol0489649

DO - 10.1021/ol0489649

M3 - Article

C2 - 15469320

AN - SCOPUS:7044284727

SN - 1523-7060

VL - 6

SP - 3671

EP - 3674

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b] azepin-8-ones

Abstract

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