Kémiai kalandozások: Színreakciók, cikloaddíciók és cikloreverziók

Translated title of the contribution: Challenges in chemistry; colour reactions, cycloadditions and cycloreversions

Research output: Contribution to journalArticle

Abstract

New colour reactions for the identification of drug compounds have been devised. For example, butazolidine is oxidized with permanganate in basic medium to azobenzene and butyric acid; after reduction and coupling, the former is transformed to a red azodye. On nitration, gluthetimide gives the p-nitrophenyl derivative and a second nitro group is substituted at position 3. With hydroxylamine in basic medium, this o-dinitro compound reacts to furnish a violet colour when the dinitro derivative is reduced to the ortho-quinoidal dialkali metal salt. Dipolar cycloadditions of BNO, ANO and DPNI to norbornane- and cyclohexane-condensed 1,3-oxazine dipolarophiles have been utilized to synthesize adducts containing 1,2,4-oxadiazole and -triazole rings. The norbornene double dipolarophiles contain both C=N and C=C bonds; for steric reasons, ketene formed in situ adds primarily to the C=C. The addition of dipoles with high steric demands can lead to a change in conformation. By means of retro Diels-Alder reactions, hetero- mono-, bi- and tricyclic compounds may be synthesized. With bifunctional reagents, norbornene amino acids and hydrazides are transformed to condensed cyclic derivatives; when these are heated, cyclopentadiene is cleaved off to give mostly new target compounds.

Original languageHungarian
Pages (from-to)143-151
Number of pages9
JournalActa Pharmaceutica Hungarica
Volume71
Issue number2
Publication statusPublished - 2001

Fingerprint

Cycloaddition Reaction
Norbornanes
Color
Cross-Linking Reagents
Oxadiazoles
Cyclopentanes
Hydroxylamine
Butyric Acid
Salts
Metals
Amino Acids
Pharmaceutical Preparations
2-norbornene
Cyclohexane
oxazine 1
1,2,4-triazole
ketene
azobenzene
permanganic acid

ASJC Scopus subject areas

  • Pharmaceutical Science

Cite this

Kémiai kalandozások : Színreakciók, cikloaddíciók és cikloreverziók. / Stájer, G.

In: Acta Pharmaceutica Hungarica, Vol. 71, No. 2, 2001, p. 143-151.

Research output: Contribution to journalArticle

@article{7bcec4c7a1904dafaa7deded29d6aea1,
title = "K{\'e}miai kalandoz{\'a}sok: Sz{\'i}nreakci{\'o}k, cikloadd{\'i}ci{\'o}k {\'e}s cikloreverzi{\'o}k",
abstract = "New colour reactions for the identification of drug compounds have been devised. For example, butazolidine is oxidized with permanganate in basic medium to azobenzene and butyric acid; after reduction and coupling, the former is transformed to a red azodye. On nitration, gluthetimide gives the p-nitrophenyl derivative and a second nitro group is substituted at position 3. With hydroxylamine in basic medium, this o-dinitro compound reacts to furnish a violet colour when the dinitro derivative is reduced to the ortho-quinoidal dialkali metal salt. Dipolar cycloadditions of BNO, ANO and DPNI to norbornane- and cyclohexane-condensed 1,3-oxazine dipolarophiles have been utilized to synthesize adducts containing 1,2,4-oxadiazole and -triazole rings. The norbornene double dipolarophiles contain both C=N and C=C bonds; for steric reasons, ketene formed in situ adds primarily to the C=C. The addition of dipoles with high steric demands can lead to a change in conformation. By means of retro Diels-Alder reactions, hetero- mono-, bi- and tricyclic compounds may be synthesized. With bifunctional reagents, norbornene amino acids and hydrazides are transformed to condensed cyclic derivatives; when these are heated, cyclopentadiene is cleaved off to give mostly new target compounds.",
author = "G. St{\'a}jer",
year = "2001",
language = "Hungarian",
volume = "71",
pages = "143--151",
journal = "Acta Pharmaceutica Hungarica",
issn = "0001-6659",
publisher = "Magyar Gyogyszereszeti Tarsasag",
number = "2",

}

TY - JOUR

T1 - Kémiai kalandozások

T2 - Színreakciók, cikloaddíciók és cikloreverziók

AU - Stájer, G.

PY - 2001

Y1 - 2001

N2 - New colour reactions for the identification of drug compounds have been devised. For example, butazolidine is oxidized with permanganate in basic medium to azobenzene and butyric acid; after reduction and coupling, the former is transformed to a red azodye. On nitration, gluthetimide gives the p-nitrophenyl derivative and a second nitro group is substituted at position 3. With hydroxylamine in basic medium, this o-dinitro compound reacts to furnish a violet colour when the dinitro derivative is reduced to the ortho-quinoidal dialkali metal salt. Dipolar cycloadditions of BNO, ANO and DPNI to norbornane- and cyclohexane-condensed 1,3-oxazine dipolarophiles have been utilized to synthesize adducts containing 1,2,4-oxadiazole and -triazole rings. The norbornene double dipolarophiles contain both C=N and C=C bonds; for steric reasons, ketene formed in situ adds primarily to the C=C. The addition of dipoles with high steric demands can lead to a change in conformation. By means of retro Diels-Alder reactions, hetero- mono-, bi- and tricyclic compounds may be synthesized. With bifunctional reagents, norbornene amino acids and hydrazides are transformed to condensed cyclic derivatives; when these are heated, cyclopentadiene is cleaved off to give mostly new target compounds.

AB - New colour reactions for the identification of drug compounds have been devised. For example, butazolidine is oxidized with permanganate in basic medium to azobenzene and butyric acid; after reduction and coupling, the former is transformed to a red azodye. On nitration, gluthetimide gives the p-nitrophenyl derivative and a second nitro group is substituted at position 3. With hydroxylamine in basic medium, this o-dinitro compound reacts to furnish a violet colour when the dinitro derivative is reduced to the ortho-quinoidal dialkali metal salt. Dipolar cycloadditions of BNO, ANO and DPNI to norbornane- and cyclohexane-condensed 1,3-oxazine dipolarophiles have been utilized to synthesize adducts containing 1,2,4-oxadiazole and -triazole rings. The norbornene double dipolarophiles contain both C=N and C=C bonds; for steric reasons, ketene formed in situ adds primarily to the C=C. The addition of dipoles with high steric demands can lead to a change in conformation. By means of retro Diels-Alder reactions, hetero- mono-, bi- and tricyclic compounds may be synthesized. With bifunctional reagents, norbornene amino acids and hydrazides are transformed to condensed cyclic derivatives; when these are heated, cyclopentadiene is cleaved off to give mostly new target compounds.

UR - http://www.scopus.com/inward/record.url?scp=0034797442&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034797442&partnerID=8YFLogxK

M3 - Article

C2 - 11862661

AN - SCOPUS:0034797442

VL - 71

SP - 143

EP - 151

JO - Acta Pharmaceutica Hungarica

JF - Acta Pharmaceutica Hungarica

SN - 0001-6659

IS - 2

ER -