Sequenced cyclizations involving intramolecular capture of alkyl-oxyaminyl radicals. Synthesis of heterocyclic compounds

Luz Marina Jaramillo-Gómez; Alix Elena Loaiza; Jaime Martin; Luz Amalia Ríos; Peng George Wang

doi:10.1016/j.tetlet.2006.03.161

Sequenced cyclizations involving intramolecular capture of alkyl-oxyaminyl radicals. Synthesis of heterocyclic compounds

Luz Marina Jaramillo-Gómez
, Alix Elena Loaiza
, Jaime Martin
, Luz Amalia Ríos
, Peng George Wang

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

14 Scopus citations

Abstract

A cascade radical cyclization process involving oxime ethers tethered to a brominated phenyl and an activated olefin moiety is described. The generated aryl radicals using tri-n-butyltin hydride react with the C{double bond, long}N bond to yield neutral alkyl-oxyaminyl radicals, which were then simultaneously captured by the activated double bond to provide heterocyclic systems with a pyrrolidinic nucleus.

Original language	English
Pages (from-to)	3909-3912
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2006.03.161
State	Published - 05 Jun 2006
Externally published	Yes

Keywords

Cascade radical cyclizations
Synthesis of N-heterocyclic compounds
Trapping of alkyl-oxyaminyl radicals

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10.1016/j.tetlet.2006.03.161

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title = "Sequenced cyclizations involving intramolecular capture of alkyl-oxyaminyl radicals. Synthesis of heterocyclic compounds",

abstract = "A cascade radical cyclization process involving oxime ethers tethered to a brominated phenyl and an activated olefin moiety is described. The generated aryl radicals using tri-n-butyltin hydride react with the C\{double bond, long\}N bond to yield neutral alkyl-oxyaminyl radicals, which were then simultaneously captured by the activated double bond to provide heterocyclic systems with a pyrrolidinic nucleus.",

keywords = "Cascade radical cyclizations, Synthesis of N-heterocyclic compounds, Trapping of alkyl-oxyaminyl radicals",

author = "Jaramillo-G{\'o}mez, \{Luz Marina\} and Loaiza, \{Alix Elena\} and Jaime Martin and R{\'i}os, \{Luz Amalia\} and Wang, \{Peng George\}",

note = "Funding Information: We thank COLCIENCIAS–(Bogot{\'a}-Colombia), for the financial support through the project 1106-05-10108, Universidad del Valle (Colombia). This work was supported in part by NSF (CH-0316806) to P.G.W.",

year = "2006",

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doi = "10.1016/j.tetlet.2006.03.161",

language = "English",

volume = "47",

pages = "3909--3912",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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TY - JOUR

T1 - Sequenced cyclizations involving intramolecular capture of alkyl-oxyaminyl radicals. Synthesis of heterocyclic compounds

AU - Jaramillo-Gómez, Luz Marina

AU - Loaiza, Alix Elena

AU - Martin, Jaime

AU - Ríos, Luz Amalia

AU - Wang, Peng George

N1 - Funding Information: We thank COLCIENCIAS–(Bogotá-Colombia), for the financial support through the project 1106-05-10108, Universidad del Valle (Colombia). This work was supported in part by NSF (CH-0316806) to P.G.W.

PY - 2006/6/5

Y1 - 2006/6/5

N2 - A cascade radical cyclization process involving oxime ethers tethered to a brominated phenyl and an activated olefin moiety is described. The generated aryl radicals using tri-n-butyltin hydride react with the C{double bond, long}N bond to yield neutral alkyl-oxyaminyl radicals, which were then simultaneously captured by the activated double bond to provide heterocyclic systems with a pyrrolidinic nucleus.

AB - A cascade radical cyclization process involving oxime ethers tethered to a brominated phenyl and an activated olefin moiety is described. The generated aryl radicals using tri-n-butyltin hydride react with the C{double bond, long}N bond to yield neutral alkyl-oxyaminyl radicals, which were then simultaneously captured by the activated double bond to provide heterocyclic systems with a pyrrolidinic nucleus.

KW - Cascade radical cyclizations

KW - Synthesis of N-heterocyclic compounds

KW - Trapping of alkyl-oxyaminyl radicals

UR - https://www.scopus.com/pages/publications/33748161340

U2 - 10.1016/j.tetlet.2006.03.161

DO - 10.1016/j.tetlet.2006.03.161

M3 - Article

AN - SCOPUS:33748161340

SN - 0040-4039

VL - 47

SP - 3909

EP - 3912

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Sequenced cyclizations involving intramolecular capture of alkyl-oxyaminyl radicals. Synthesis of heterocyclic compounds

Abstract

Keywords

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