Syntheses and transformations of α-azido ketones and related derivatives

T. Patonay, Krisztina Kónya, Éva Juhász-Tóth

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Organic azides are known and utilized in the synthetic organic chemistry as amine precursors, potential sources of nitrenes, dipoles useful in 1,3-dipolar cycloadditions and starting materials of phosphoranes for a long time, and their literature has been overviewed by several authors. On the other hand, there are some special subclasses within the azides which possess peculiar and interesting properties differing from those of the majority and offering extra synthetic possibilities. In this critical review we wish to give an exhaustive overview on the synthesis and synthetic potential of α-azido ketones and related systems, an underestimated group of compounds. The enhanced acidity of the α-hydrogen offers various new synthetic applications including the creation of a new C-C bond, while the joint presence of the carbonyl and vinyl functions of α-azido-α,β-unsaturated ketones results in a special reactivity, too. Chemo- and stereoselectivity issues also represent important points which are discussed in detail. Finally, the usefulness of the titled derivatives in the synthesis of various heterocycles is reviewed (273 references).

Original languageEnglish
Pages (from-to)2797-2847
Number of pages51
JournalChemical Society Reviews
Volume40
Issue number5
DOIs
Publication statusPublished - May 2011

Fingerprint

Azides
Ketones
Phosphoranes
Derivatives
Stereoselectivity
Cycloaddition
Acidity
Amines
Hydrogen
Organic Chemistry

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Syntheses and transformations of α-azido ketones and related derivatives. / Patonay, T.; Kónya, Krisztina; Juhász-Tóth, Éva.

In: Chemical Society Reviews, Vol. 40, No. 5, 05.2011, p. 2797-2847.

Research output: Contribution to journalArticle

Patonay, T. ; Kónya, Krisztina ; Juhász-Tóth, Éva. / Syntheses and transformations of α-azido ketones and related derivatives. In: Chemical Society Reviews. 2011 ; Vol. 40, No. 5. pp. 2797-2847.
@article{f9ccb691a7c1422eb8a15a85dff02c4e,
title = "Syntheses and transformations of α-azido ketones and related derivatives",
abstract = "Organic azides are known and utilized in the synthetic organic chemistry as amine precursors, potential sources of nitrenes, dipoles useful in 1,3-dipolar cycloadditions and starting materials of phosphoranes for a long time, and their literature has been overviewed by several authors. On the other hand, there are some special subclasses within the azides which possess peculiar and interesting properties differing from those of the majority and offering extra synthetic possibilities. In this critical review we wish to give an exhaustive overview on the synthesis and synthetic potential of α-azido ketones and related systems, an underestimated group of compounds. The enhanced acidity of the α-hydrogen offers various new synthetic applications including the creation of a new C-C bond, while the joint presence of the carbonyl and vinyl functions of α-azido-α,β-unsaturated ketones results in a special reactivity, too. Chemo- and stereoselectivity issues also represent important points which are discussed in detail. Finally, the usefulness of the titled derivatives in the synthesis of various heterocycles is reviewed (273 references).",
author = "T. Patonay and Krisztina K{\'o}nya and {\'E}va Juh{\'a}sz-T{\'o}th",
year = "2011",
month = "5",
doi = "10.1039/c0cs00101e",
language = "English",
volume = "40",
pages = "2797--2847",
journal = "Chemical Society Reviews",
issn = "0306-0012",
publisher = "Royal Society of Chemistry",
number = "5",

}

TY - JOUR

T1 - Syntheses and transformations of α-azido ketones and related derivatives

AU - Patonay, T.

AU - Kónya, Krisztina

AU - Juhász-Tóth, Éva

PY - 2011/5

Y1 - 2011/5

N2 - Organic azides are known and utilized in the synthetic organic chemistry as amine precursors, potential sources of nitrenes, dipoles useful in 1,3-dipolar cycloadditions and starting materials of phosphoranes for a long time, and their literature has been overviewed by several authors. On the other hand, there are some special subclasses within the azides which possess peculiar and interesting properties differing from those of the majority and offering extra synthetic possibilities. In this critical review we wish to give an exhaustive overview on the synthesis and synthetic potential of α-azido ketones and related systems, an underestimated group of compounds. The enhanced acidity of the α-hydrogen offers various new synthetic applications including the creation of a new C-C bond, while the joint presence of the carbonyl and vinyl functions of α-azido-α,β-unsaturated ketones results in a special reactivity, too. Chemo- and stereoselectivity issues also represent important points which are discussed in detail. Finally, the usefulness of the titled derivatives in the synthesis of various heterocycles is reviewed (273 references).

AB - Organic azides are known and utilized in the synthetic organic chemistry as amine precursors, potential sources of nitrenes, dipoles useful in 1,3-dipolar cycloadditions and starting materials of phosphoranes for a long time, and their literature has been overviewed by several authors. On the other hand, there are some special subclasses within the azides which possess peculiar and interesting properties differing from those of the majority and offering extra synthetic possibilities. In this critical review we wish to give an exhaustive overview on the synthesis and synthetic potential of α-azido ketones and related systems, an underestimated group of compounds. The enhanced acidity of the α-hydrogen offers various new synthetic applications including the creation of a new C-C bond, while the joint presence of the carbonyl and vinyl functions of α-azido-α,β-unsaturated ketones results in a special reactivity, too. Chemo- and stereoselectivity issues also represent important points which are discussed in detail. Finally, the usefulness of the titled derivatives in the synthesis of various heterocycles is reviewed (273 references).

UR - http://www.scopus.com/inward/record.url?scp=79954573197&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79954573197&partnerID=8YFLogxK

U2 - 10.1039/c0cs00101e

DO - 10.1039/c0cs00101e

M3 - Article

VL - 40

SP - 2797

EP - 2847

JO - Chemical Society Reviews

JF - Chemical Society Reviews

SN - 0306-0012

IS - 5

ER -