Synthesis and Characterizations of Some New 4H-1,2,4-Triazole Derivatives

Neslihan DEMİRBAŞ; Ahmet DEMİRBAŞ; Şule CEYLAN; Deniz ŞAHİN

Makale detayları

Synthesis and Characterizations of Some New 4H-1,2,4-Triazole Derivatives

Yazarlar:

Neslihan DEMİRBAŞ | Ahmet DEMİRBAŞ | Şule CEYLAN | Deniz ŞAHİN

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2008 Vol.32 Issue 1, pp.1-8

Belge Tipi:

Makale

Yayın Tarihi:

12/2007

Belge Dili:

İngilizce

Document ID (Org No.):

2000728549

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

3-[(5-Amino-1,3,4-thiadiazol-2-yl)methyl]-4-ethoxycarbonylamino-5-alkyl-4H-1,2,4-triazoles  (2a,b) were obtained from the reaction of  3-cyanomethyl-5-alkyl-4-ethoxycarbonylamino-4H-1,2,4-triazoles (1a,b)  with thiosemicarbazide in the presence of trifluoroacetic acid.  The  treatment of the obtained compounds (2a,b) with acetic anhydride for 1  h afforded  3-[(5-acetylamino-1,3,4-thiadiazol-2-yl)methyl]-4-ethoxycarbonylamino-5-alkyl-4H-1,2,4-triazoles  (3a,b).  The synthesis of  4-ethoxycarbonylamino-3-[(2,3-dihydro-1,3-benzoxazol-2-yl)methyl]-5-(4-methylbenzyl)-4H-1,2,4-triazole  (4) was performed by the treatment of  3-[(5-acetylamino-1,3,4-thiadiazol-2-yl)methyl]-4-ethoxycarbonylamino-5-(4-methylbenzyl)-4H-1,2,4-triazole  (3a) with o-aminophenol under nitrogen atmosphere for 50 h.  The  reaction of compounds 1a,b with salicylaldehyde in the presence of  sodium ethoxide yielded  2-{4-[(ethoxycarbonyl)amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-(2-hydroxyphenyl)-acrylonitriles  (5a,b).  The acetylations of compounds 5a,b with acetic anhydride for  5 h resulted in the formation of  2-{4-[acetyl(ethoxycarbonyl)amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-[2-(acetyloxy)phenyl]-acrylic  acids (6a,b).  On the other hand, the treatment of compounds 5a,b with  methyl iodide in the presence of NaOH produced 2-{4-[(ethoxycarbonyl)  amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-(2-methoxyphenyl)acrylic  acids (7a,b).

 

3-[(5-Amino-1,3,4-thiadiazol-2-yl)methyl]-4-ethoxycarbonylamino-5-alkyl-4H-1,2,4-triazoles  (2a,b) were obtained from the reaction of  3-cyanomethyl-5-alkyl-4-ethoxycarbonylamino-4H-1,2,4-triazoles (1a,b)  with thiosemicarbazide in the presence of trifluoroacetic acid.  The  treatment of the obtained compounds (2a,b) with acetic anhydride for 1  h afforded  3-[(5-acetylamino-1,3,4-thiadiazol-2-yl)methyl]-4-ethoxycarbonylamino-5-alkyl-4H-1,2,4-triazoles  (3a,b).  The synthesis of  4-ethoxycarbonylamino-3-[(2,3-dihydro-1,3-benzoxazol-2-yl)methyl]-5-(4-methylbenzyl)-4H-1,2,4-triazole  (4) was performed by the treatment of  3-[(5-acetylamino-1,3,4-thiadiazol-2-yl)methyl]-4-ethoxycarbonylamino-5-(4-methylbenzyl)-4H-1,2,4-triazole  (3a) with o-aminophenol under nitrogen atmosphere for 50 h.  The  reaction of compounds 1a,b with salicylaldehyde in the presence of  sodium ethoxide yielded  2-{4-[(ethoxycarbonyl)amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-(2-hydroxyphenyl)-acrylonitriles  (5a,b).  The acetylations of compounds 5a,b with acetic anhydride for  5 h resulted in the formation of  2-{4-[acetyl(ethoxycarbonyl)amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-[2-(acetyloxy)phenyl]-acrylic  acids (6a,b).  On the other hand, the treatment of compounds 5a,b with  methyl iodide in the presence of NaOH produced 2-{4-[(ethoxycarbonyl)  amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-(2-methoxyphenyl)acrylic  acids (7a,b).

Makale detayları

Synthesis and Characterizations of Some New 4H-1,2,4-Triazole Derivatives

Yazarlar: Neslihan DEMİRBAŞ | Ahmet DEMİRBAŞ | Şule CEYLAN | Deniz ŞAHİN

Yayıncı: TUBITAK

Ana Başlıklar: Uygulamalı fizik

Dergi: Turkish Journal of Chemistry 2008 Vol.32 Issue 1, pp.1-8

Belge Tipi: Makale

Yayın Tarihi: 12/2007

Belge Dili: İngilizce

Document ID (Org No.): 2000728549

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Neslihan DEMİRBAŞ | Ahmet DEMİRBAŞ | Şule CEYLAN | Deniz ŞAHİN

Yayıncı:

TUBITAK

Ana Başlıklar:

Uygulamalı fizik

Dergi:

Turkish Journal of Chemistry 2008 Vol.32 Issue 1, pp.1-8

Belge Tipi:

Makale

Yayın Tarihi:

12/2007

Belge Dili:

İngilizce

Document ID (Org No.):

2000728549

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527