The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction

Fraser Macleod; Stuart Lang; John A. Murphy

doi:10.1055/s-0029-1219340

The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction

Fraser Macleod, Stuart Lang, John A. Murphy

Pure And Applied Chemistry

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

22 Citations (Scopus)

128 Downloads (Pure)

Abstract

2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aubé-Schmidt reaction, sometimes in excellent yield, and solvolysis yields derivatives of medium-ring amines. Attempts to divert the Schmidt reaction with an arene-mediated fragmentation of the normal Schmidt intermediate have led to an initial example.

Original language	English
Pages (from-to)	529-534
Number of pages	6
Journal	Synlett
Volume	2010
Issue number	4
DOIs	https://doi.org/10.1055/s-0029-1219340
Publication status	Published - Mar 2010

Keywords

Aubé-Schmidt
rearrangement
azide
heterocycle
bridged amide
medium-ring amine
medium-ring amide

Access to Document

10.1055/s-0029-1219340

Cite this

@article{ad393e57398c49c09143751aa8501e06,

title = "The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aub{\'e}-Schmidt reaction",

abstract = "2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aub{\'e}-Schmidt reaction, sometimes in excellent yield, and solvolysis yields derivatives of medium-ring amines. Attempts to divert the Schmidt reaction with an arene-mediated fragmentation of the normal Schmidt intermediate have led to an initial example.",

keywords = "Aub{\'e}-Schmidt, rearrangement, azide, heterocycle, bridged amide, medium-ring amine, medium-ring amide",

author = "Fraser Macleod and Stuart Lang and Murphy, {John A.}",

year = "2010",

month = mar,

doi = "10.1055/s-0029-1219340",

language = "English",

volume = "2010",

pages = "529--534",

journal = "Synlett",

issn = "0936-5214",

number = "4",

}

TY - JOUR

T1 - The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction

AU - Macleod, Fraser

AU - Lang, Stuart

AU - Murphy, John A.

PY - 2010/3

Y1 - 2010/3

N2 - 2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aubé-Schmidt reaction, sometimes in excellent yield, and solvolysis yields derivatives of medium-ring amines. Attempts to divert the Schmidt reaction with an arene-mediated fragmentation of the normal Schmidt intermediate have led to an initial example.

AB - 2-(2-Azidoethyl)cycloalkanones afford bridged lactams in the Aubé-Schmidt reaction, sometimes in excellent yield, and solvolysis yields derivatives of medium-ring amines. Attempts to divert the Schmidt reaction with an arene-mediated fragmentation of the normal Schmidt intermediate have led to an initial example.

KW - Aubé-Schmidt

KW - rearrangement

KW - azide

KW - heterocycle

KW - bridged amide

KW - medium-ring amine

KW - medium-ring amide

UR - http://www.scopus.com/inward/record.url?scp=77955352481&partnerID=8YFLogxK

U2 - 10.1055/s-0029-1219340

DO - 10.1055/s-0029-1219340

M3 - Article

SN - 0936-5214

VL - 2010

SP - 529

EP - 534

JO - Synlett

JF - Synlett

IS - 4

ER -

The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Cite this

The 2-(2-Azidoethyl)cycloalkanone strategy for bridged amides and medium-sized cyclic amine derivatives in the Aubé-Schmidt reaction

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

Cite this