Synthesis of medium ring heterocycles using an intramolecular Heck reaction

Leggy A. Arnold; Wenchen Luo; R. Kiplin Guy

doi:10.1021/ol0487884

Synthesis of medium ring heterocycles using an intramolecular Heck reaction

Leggy A. Arnold, Wenchen Luo, R. Kiplin Guy

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

98 Scopus citations

Abstract

(Equation Presented) Historically, general convergent syntheses of medium ring heterocycles have been difficult to develop. Herein, we describe the synthesis of five classes of heterocycles: dihydrodibenzo[b,f]azepine, -oxocine, and -thiocine and dibenzo[b,f]azepine and -oxepine using a strategy of alkylation followed by highly selective intramolecular Heck arylation reaction. The hetero-tricyclic compounds were available in only two steps starting from commercially available starting materials.

Original language	English
Pages (from-to)	3005-3007
Number of pages	3
Journal	Organic Letters
Volume	6
Issue number	17
DOIs	https://doi.org/10.1021/ol0487884
State	Published - Aug 19 2004

Funding

Funders	Funder number
National Institute of Diabetes and Digestive and Kidney Diseases	R01DK058080

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol0487884

Cite this

@article{6eb8a27574e5471d990617306835d740,

title = "Synthesis of medium ring heterocycles using an intramolecular Heck reaction",

abstract = "(Equation Presented) Historically, general convergent syntheses of medium ring heterocycles have been difficult to develop. Herein, we describe the synthesis of five classes of heterocycles: dihydrodibenzo[b,f]azepine, -oxocine, and -thiocine and dibenzo[b,f]azepine and -oxepine using a strategy of alkylation followed by highly selective intramolecular Heck arylation reaction. The hetero-tricyclic compounds were available in only two steps starting from commercially available starting materials.",

author = "Arnold, {Leggy A.} and Wenchen Luo and Guy, {R. Kiplin}",

year = "2004",

month = aug,

day = "19",

doi = "10.1021/ol0487884",

language = "English",

volume = "6",

pages = "3005--3007",

number = "17",

}

TY - JOUR

T1 - Synthesis of medium ring heterocycles using an intramolecular Heck reaction

AU - Arnold, Leggy A.

AU - Luo, Wenchen

AU - Guy, R. Kiplin

PY - 2004/8/19

Y1 - 2004/8/19

N2 - (Equation Presented) Historically, general convergent syntheses of medium ring heterocycles have been difficult to develop. Herein, we describe the synthesis of five classes of heterocycles: dihydrodibenzo[b,f]azepine, -oxocine, and -thiocine and dibenzo[b,f]azepine and -oxepine using a strategy of alkylation followed by highly selective intramolecular Heck arylation reaction. The hetero-tricyclic compounds were available in only two steps starting from commercially available starting materials.

AB - (Equation Presented) Historically, general convergent syntheses of medium ring heterocycles have been difficult to develop. Herein, we describe the synthesis of five classes of heterocycles: dihydrodibenzo[b,f]azepine, -oxocine, and -thiocine and dibenzo[b,f]azepine and -oxepine using a strategy of alkylation followed by highly selective intramolecular Heck arylation reaction. The hetero-tricyclic compounds were available in only two steps starting from commercially available starting materials.

UR - http://www.scopus.com/inward/record.url?scp=4444308033&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4444308033&partnerID=8YFLogxK

U2 - 10.1021/ol0487884

DO - 10.1021/ol0487884

M3 - Article

C2 - 15330669

AN - SCOPUS:4444308033

SN - 1523-7060

VL - 6

SP - 3005

EP - 3007

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Synthesis of medium ring heterocycles using an intramolecular Heck reaction

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this