Flash vacuum pyrolysis of N-alkenylbenzotriazoles and N-alkenylisoxazolones

Matthew Cox; Fariba Heidarizadeh; Rolf H Pragei

doi:10.1071/CH00098

Flash vacuum pyrolysis of N-alkenylbenzotriazoles and N-alkenylisoxazolones

Matthew Cox, Fariba Heidarizadeh, Rolf H Pragei

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

28 Citations (Scopus)

Abstract

The flash vacuum pyrolysis of 1-(2-ethoxycarbonylethenyl)benzotriazole has been reinvestigated, and the processes leading to the formation of ethyl indole-3-carboxylate and 2-ethoxyquinolin-4(1H)-one elucidated. Similar pathways are followed in the flash vacuum pyrolysis of the corresponding benzisoxazolone. Some N-ethenylisoxazolones have been pyrolysed to form pyrroles, but rearrangement of the intermediate carbenes may be observed. Photolysis of the isoxazolones gives carbenes that may be captured by solvent or give pyrroles.

Original language	English
Pages (from-to)	665-671
Number of pages	7
Journal	Australian Journal of Chemistry
Volume	53
Issue number	8
DOIs	https://doi.org/10.1071/CH00098
Publication status	Published - 2000

Keywords

Carbenes
Dipolar cycloaddition
Diradicals
Indoles
Pyrroles
Quinolin-4-ones

Access to Document

10.1071/CH00098Licence: In Copyright

Cite this

@article{2967960325b544288af5d95d9589ca86,

title = "Flash vacuum pyrolysis of N-alkenylbenzotriazoles and N-alkenylisoxazolones",

abstract = "The flash vacuum pyrolysis of 1-(2-ethoxycarbonylethenyl)benzotriazole has been reinvestigated, and the processes leading to the formation of ethyl indole-3-carboxylate and 2-ethoxyquinolin-4(1H)-one elucidated. Similar pathways are followed in the flash vacuum pyrolysis of the corresponding benzisoxazolone. Some N-ethenylisoxazolones have been pyrolysed to form pyrroles, but rearrangement of the intermediate carbenes may be observed. Photolysis of the isoxazolones gives carbenes that may be captured by solvent or give pyrroles.",

keywords = "Carbenes, Dipolar cycloaddition, Diradicals, Indoles, Pyrroles, Quinolin-4-ones",

author = "Matthew Cox and Fariba Heidarizadeh and Pragei, {Rolf H}",

year = "2000",

doi = "10.1071/CH00098",

language = "English",

volume = "53",

pages = "665--671",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "CSIRO Publishing",

number = "8",

}

TY - JOUR

T1 - Flash vacuum pyrolysis of N-alkenylbenzotriazoles and N-alkenylisoxazolones

AU - Cox, Matthew

AU - Heidarizadeh, Fariba

AU - Pragei, Rolf H

PY - 2000

Y1 - 2000

N2 - The flash vacuum pyrolysis of 1-(2-ethoxycarbonylethenyl)benzotriazole has been reinvestigated, and the processes leading to the formation of ethyl indole-3-carboxylate and 2-ethoxyquinolin-4(1H)-one elucidated. Similar pathways are followed in the flash vacuum pyrolysis of the corresponding benzisoxazolone. Some N-ethenylisoxazolones have been pyrolysed to form pyrroles, but rearrangement of the intermediate carbenes may be observed. Photolysis of the isoxazolones gives carbenes that may be captured by solvent or give pyrroles.

AB - The flash vacuum pyrolysis of 1-(2-ethoxycarbonylethenyl)benzotriazole has been reinvestigated, and the processes leading to the formation of ethyl indole-3-carboxylate and 2-ethoxyquinolin-4(1H)-one elucidated. Similar pathways are followed in the flash vacuum pyrolysis of the corresponding benzisoxazolone. Some N-ethenylisoxazolones have been pyrolysed to form pyrroles, but rearrangement of the intermediate carbenes may be observed. Photolysis of the isoxazolones gives carbenes that may be captured by solvent or give pyrroles.

KW - Carbenes

KW - Dipolar cycloaddition

KW - Diradicals

KW - Indoles

KW - Pyrroles

KW - Quinolin-4-ones

UR - http://www.scopus.com/inward/record.url?scp=0142229710&partnerID=8YFLogxK

U2 - 10.1071/CH00098

DO - 10.1071/CH00098

M3 - Article

AN - SCOPUS:0142229710

SN - 0004-9425

VL - 53

SP - 665

EP - 671

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 8

ER -

Flash vacuum pyrolysis of N-alkenylbenzotriazoles and N-alkenylisoxazolones

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this