4- Hidroksimetilfenilbutazonun Baz ı Türevleri I

Hayriye AMAL; Süheylâ BAYKARA

doi:https://doi.org/10.1501/Eczfak_0000000254

Article Details

4- Hidroksimetilfenilbutazonun Baz ı Türevleri I

Authors:

Hayriye AMAL | Süheylâ BAYKARA

Publisher:

Ankara University

Journal:

Journal of Faculty of Pharmacy of Ankara University 1979 Vol.9 Issue 1, pp.0-0

Document Type:

Article

Publication Date:

5/1979

Document Language:

Turkish

Document ID (Org No.):

2000868560

Frequency:

Tri-annual

eISSN:

2564-6524

pISSN:

1015-3918

DOI:

https://doi.org/10.1501/Eczfak_0000000254

Abstract:

 

In this work Mannich bases of phenylbutazone and urethanes
 of 4-hydroxymethyphenylbutazone, which is an intermediate product
 of Mannich reaction, were prepared.
 In the Mannich condensation of phenylbutazone with formaldehyde
 and 4-aminoantipyrine or 1,3-dipheny1-4-formimidoy1-5-
 pyrazolone, N,N-bis (4'-phenylbutazonylemethyl)- 4-amino- 1-pheny1-2,3-dirnethy1-5-pyrazolone
 (I) and 4-[N-(1,2-dihpeny1-4-
 buty 1-3, 5-dioxopyraz olidine-4-meth ylene) ] formimidoy1-1,3-dipheny1-5-pyrazolone
 (II) were obtained. The reaction was performed in
 two ways. In the first one, phenylbutazone was reacted with formaldehyde
 and the appropriate amine, at the same time. In the second
 one 4-hydroxymethylphenylbutazone was prepared and then reacted
 with amine component; both reactions gave the same Mannich.
 bases. Since pheylbutazone has a stronger nucleophyllic character
 than the amine component, the reaction goes through 4-hydroxymethylpenylbutazone.
 On the other band, 4-hydroxymethylphenylbutazone was reacted
 with ethylisocynate or naphthylisocyanate and 4(N-ethyl)
 carbamoyloxymethy1-4-buty1-1,2-diphenyl-3,5-dioxopyrazolidine
 (III) and 4-[N(z-naphthyl) ] carbamoyloxymethy1-4-but1-1,2-
 dipheny1-3,5-dioxopyrazolidine (IV) were obtained.
 The structure of the mentioned compounds were proved by
 UV, IR and NMR spectroscopy and elemantary analysis. Mass
 spectrum of one selected derivative were taken, moleculer ion peak
 and spesific fragmentation of phenylbutazone derivatives were also
 observed.

 

Bu çalışmada, fenilbutazonun baz ı Mannich bazları ve bu reaksiyonda
 bir ara ürün olan 4-hidroksimetilfenilbutazonun baz ı
 üretanları hazırlanmış tır. Fenilbutazon, formaldehid ve 4-aminoantipirin
 veya 1,3-difeni1-4-formimidoil-5-pirazolon ile yap ılan
 Mannich kondensasyonundan N,N-bis(4'-fenilbutazonilmetil)-4-
 amino-1-feni1-2,3-dimetil-5-pirazolon (I) ve 4-[N-(1,2-difenil
 4-butil-3,5-dioksopirazolidin-4-metilen] formimidoil-1,3-difenilpirazolon
 (II) elde edilmi ştir. Reaksiyon iki ş ekilde yürütülmüş , birinci
 metodda fenilbutazon, amin ve formaldehid ayn ı anda ortama
 ilave edilerek çalışı lmış ; ikinci metodda ise 4-hidroksimetilfenilbutazon,
 amin komponentiyle reaksiyona sokulmu ş ; her iki metod
 da aynı ürünü vermi ştir. Fenilbutazon, kullan ılan aminlerden daha
 kuvvetli nükleofil olduğundan reaksiyonun 4-hidroksimetilfenilbutazon
 üzerinden yürüdü ğü kanıtlanmış tır.
 Bundan başka, 4-hidroksimetilfenilbutazon etilisosiyanat veya
 naffilisosiyanat ile reaksiyona sokularak üretan yap ısındaki 4(Netil)karbamoiloksimetil-4-bu,i1-1,2-difeni1-3,5dioksopirazolidin
 (III)
 ve 4-[ (N-(oc-naftil) ]karba ınoiloksimetil-4-butil-1,2-difeni1-3,5-dioksopirazolidin
 (IV) kazan ı lmıştır.
 Bütün maddelerin yapıları elementel analiz, UV, IR, NMR
 bulguları yardımıyla aydı nlatılmış ; ayrı ca seçilen bir türevin kütle
 spektrumu alı nmış ve spektrumda moleküler iyon piki yan ında fenilbutazon
 türevlerine özgü fragmentler saptanm ış tır.

Article Details

4- Hidroksimetilfenilbutazonun Baz ı Türevleri I

Authors: Hayriye AMAL | Süheylâ BAYKARA

Publisher: Ankara University

Journal: Journal of Faculty of Pharmacy of Ankara University 1979 Vol.9 Issue 1, pp.0-0

Document Type: Article

Publication Date: 5/1979

Document Language: Turkish

Document ID (Org No.): 2000868560

Frequency: Tri-annual

eISSN: 2564-6524

pISSN: 1015-3918

DOI: https://doi.org/10.1501/Eczfak_0000000254

Issues

Authors:

Hayriye AMAL | Süheylâ BAYKARA

Publisher:

Ankara University

Journal:

Journal of Faculty of Pharmacy of Ankara University 1979 Vol.9 Issue 1, pp.0-0

Document Type:

Article

Publication Date:

5/1979

Document Language:

Turkish

Document ID (Org No.):

2000868560

Frequency:

Tri-annual

eISSN:

2564-6524

pISSN:

1015-3918

DOI:

https://doi.org/10.1501/Eczfak_0000000254