Investigation of the reaction of o-aminonitriles with ketones: A new modification of Friedländer reaction and structures of its products

Jiarong Li; Lijun Zhang; Daxin Shi; Qing Li; Dong Wang; Chunxia Wang; Qi Zhang; Ling Zhang; Yanqiu Fan

doi:10.1055/s-2007-1000841

Investigation of the reaction of o-aminonitriles with ketones: A new modification of Friedländer reaction and structures of its products

Jiarong Li^*, Lijun Zhang, Daxin Shi, Qing Li, Dong Wang, Chunxia Wang, Qi Zhang, Ling Zhang, Yanqiu Fan

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

46 Citations (Scopus)

Abstract

A new modification of the Friedländer reaction is described and the new byproduct obtained from the reaction of o-aminonitriles and ketones was found to be 2,3-dihydroquinazolin-4(1H)-one. The mechanism probably involved the formation of an intermediate oxazine, via the Pinner reaction and its transformation into new products via the Dimroth rearrangement.

Original language	English
Pages (from-to)	233-236
Number of pages	4
Journal	Synlett
Issue number	2
DOIs	https://doi.org/10.1055/s-2007-1000841
Publication status	Published - 22 Jan 2008

Keywords

Cyclizations
Friedländer reactions
Molecular recognition
Rearrangements
Spiro compounds

Access to Document

10.1055/s-2007-1000841

Cite this

@article{baa76392687a4534be9e1d3f3d9801f8,

title = "Investigation of the reaction of o-aminonitriles with ketones: A new modification of Friedl{\"a}nder reaction and structures of its products",

abstract = "A new modification of the Friedl{\"a}nder reaction is described and the new byproduct obtained from the reaction of o-aminonitriles and ketones was found to be 2,3-dihydroquinazolin-4(1H)-one. The mechanism probably involved the formation of an intermediate oxazine, via the Pinner reaction and its transformation into new products via the Dimroth rearrangement.",

keywords = "Cyclizations, Friedl{\"a}nder reactions, Molecular recognition, Rearrangements, Spiro compounds",

author = "Jiarong Li and Lijun Zhang and Daxin Shi and Qing Li and Dong Wang and Chunxia Wang and Qi Zhang and Ling Zhang and Yanqiu Fan",

year = "2008",

month = jan,

day = "22",

doi = "10.1055/s-2007-1000841",

language = "English",

pages = "233--236",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "2",

}

TY - JOUR

T1 - Investigation of the reaction of o-aminonitriles with ketones

T2 - A new modification of Friedländer reaction and structures of its products

AU - Li, Jiarong

AU - Zhang, Lijun

AU - Shi, Daxin

AU - Li, Qing

AU - Wang, Dong

AU - Wang, Chunxia

AU - Zhang, Qi

AU - Zhang, Ling

AU - Fan, Yanqiu

PY - 2008/1/22

Y1 - 2008/1/22

N2 - A new modification of the Friedländer reaction is described and the new byproduct obtained from the reaction of o-aminonitriles and ketones was found to be 2,3-dihydroquinazolin-4(1H)-one. The mechanism probably involved the formation of an intermediate oxazine, via the Pinner reaction and its transformation into new products via the Dimroth rearrangement.

AB - A new modification of the Friedländer reaction is described and the new byproduct obtained from the reaction of o-aminonitriles and ketones was found to be 2,3-dihydroquinazolin-4(1H)-one. The mechanism probably involved the formation of an intermediate oxazine, via the Pinner reaction and its transformation into new products via the Dimroth rearrangement.

KW - Cyclizations

KW - Friedländer reactions

KW - Molecular recognition

KW - Rearrangements

KW - Spiro compounds

UR - http://www.scopus.com/inward/record.url?scp=38949159951&partnerID=8YFLogxK

U2 - 10.1055/s-2007-1000841

DO - 10.1055/s-2007-1000841

M3 - Article

AN - SCOPUS:38949159951

SN - 0936-5214

SP - 233

EP - 236

JO - Synlett

JF - Synlett

IS - 2

ER -

Investigation of the reaction of o-aminonitriles with ketones: A new modification of Friedländer reaction and structures of its products

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this