Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives

Seda FANDAKLI; Serap BAŞOĞLU; Hakan BEKTAŞ; Meltem YOLAL

doi:https://doi.org/10.3906/yer-1207-3

Makale detayları

Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives

Yazarlar:

Seda FANDAKLI | Serap BAŞOĞLU | Hakan BEKTAŞ | Meltem YOLAL

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2012 Vol.36 Issue 4, pp.567-582

Belge Tipi:

Makale

Yayın Tarihi:

3/2012

Belge Dili:

İngilizce

Document ID (Org No.):

2000727589

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/yer-1207-3

Özet:

 

Ethyl[4-arylmethyleneamino-3-(4-metylphenyl)-5-oxo-4,5-dihydro-  1H-1,2,4-triazole-1-yl]acetates (3a-e and 10a-d) were obtained  starting from 4-amino-2,4-dihydro-3H-1,2,4-triazol-3-ones (1 and 9) in  2 steps.  The treatment of 3a-e with NaBH4 resulted in the formation  of 3 kinds of product incorporating carboxcilic acid (4a-c) or alcohol  (5a-e) functionality.  [4-{[(4-Methoxyphenyl)methylene]amino}- and  4-{[pyridin-4-ylmethylene]amino}-3-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-  1,2,4-triazole-1-yl] acetic acids (6a, 6e) were obtained by the  hydrolysis of the corresponding esters (5a-5e).  The treatment of 6a  with NaBH4 caused the reduction of only the imine bond; the carboxyl  group remained unchanged.  Then this carboxylic acid was converted to  the corresponding hydrazide (8) in 2 steps by reaction with ethanol  and hydrazine hydrate, respectively.  The synthesis of Mannich bases  was performed by the reaction of the corresponding 1,2,4-triazoles  containing an imine group (10a-d) with several primary or secondary  amines including morpholine or piperazine nucleus.  All newly synthesized compounds were screened for their antimicrobial   activity. The antimicrobial activity study revealed that the Mannich bases   (11-16) showed good activity against the test microorganisms as   compared with ampicillin.

 

Ethyl[4-arylmethyleneamino-3-(4-metylphenyl)-5-oxo-4,5-dihydro-  1H-1,2,4-triazole-1-yl]acetates (3a-e and 10a-d) were obtained  starting from 4-amino-2,4-dihydro-3H-1,2,4-triazol-3-ones (1 and 9) in  2 steps.  The treatment of 3a-e with NaBH4 resulted in the formation  of 3 kinds of product incorporating carboxcilic acid (4a-c) or alcohol  (5a-e) functionality.  [4-{[(4-Methoxyphenyl)methylene]amino}- and  4-{[pyridin-4-ylmethylene]amino}-3-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-  1,2,4-triazole-1-yl] acetic acids (6a, 6e) were obtained by the  hydrolysis of the corresponding esters (5a-5e).  The treatment of 6a  with NaBH4 caused the reduction of only the imine bond; the carboxyl  group remained unchanged.  Then this carboxylic acid was converted to  the corresponding hydrazide (8) in 2 steps by reaction with ethanol  and hydrazine hydrate, respectively.  The synthesis of Mannich bases  was performed by the reaction of the corresponding 1,2,4-triazoles  containing an imine group (10a-d) with several primary or secondary  amines including morpholine or piperazine nucleus.  All newly synthesized compounds were screened for their antimicrobial   activity. The antimicrobial activity study revealed that the Mannich bases   (11-16) showed good activity against the test microorganisms as   compared with ampicillin.

Makale detayları

Reduction, Mannich reaction, and antimicrobial activity evaluation of some new 1,2,4-triazol-3-one derivatives

Yazarlar: Seda FANDAKLI | Serap BAŞOĞLU | Hakan BEKTAŞ | Meltem YOLAL

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2012 Vol.36 Issue 4, pp.567-582

Belge Tipi: Makale

Yayın Tarihi: 3/2012

Belge Dili: İngilizce

Document ID (Org No.): 2000727589

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/yer-1207-3

Sayı

Yazarlar:

Seda FANDAKLI | Serap BAŞOĞLU | Hakan BEKTAŞ | Meltem YOLAL

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2012 Vol.36 Issue 4, pp.567-582

Belge Tipi:

Makale

Yayın Tarihi:

3/2012

Belge Dili:

İngilizce

Document ID (Org No.):

2000727589

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/yer-1207-3