A new direct synthetic access to 4-amino-2-N-(glycosyl/propyl)-1,2,4-triazole-3-thiones via hydrazinolysis of 3-N-((acylated glycosyl)/allyl)-1,3,4-oxadiazole-2-thiones

被引：8
作者：
Boraei, Ahmed T. A. [1 ]
机构：
[1] Suez Canal Univ, Fac Sci, Dept Chem, Ismailia, Egypt
来源：
ARKIVOC | 2016年
关键词：
Hydrazinolysis; 1,3,4-oxadiazole-2-thione; 1,2,4-triazolethione; thio-aza-Claisen rearrangement; 1,2,4-TRIAZOLE DERIVATIVES; ANTIMICROBIAL AGENTS; ACID;
D O I：
10.3998/ark.5550190.p009.399
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hydrazinolysis of 3-N-alkyl-1,3,4-oxadiazole-2-thiones yielded 2-N-alkyl-4-amino-1,2,4-triazole-2-thiones in a straightforward new direct procedure. Whereas, hydrazinolysis of alkylsulfanyl-1,3,4-oxadiazole derivatives resulted in the opening of the oxadiazole ring and loss of the alkyl moiety, instead of a nucleophilic substitution at the electrophilic carbon or triazole formation. Thio-aza-Claisen rearrangement of the allyl moiety in 4-amino-1,2,4-triazole was successfully achieved by fusion at atmospheric pressure in the absence of solvents and catalysts.
引用
收藏
页码：71 / 81
页数：11
相关论文
共 25 条
[1]   Synthesis and antiviral evaluation of novel 5-(N-Arylaminomethyl-1,3,4-oxadiazol-2-yl)hydrazines and their sugars, 1,2,4-triazoles, tetrazolles and pyrazolyl derivatives [J].
Abdel-Aal, Mohammed T. ;
El-Sayed, Waled A. ;
El-Kosy, Salah M. ;
El-Ashry, El Sayed H. .
ARCHIV DER PHARMAZIE, 2008, 341 (05) :307-313
[2]   Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives [J].
Aggarwal, Nisha ;
Kumar, Rajesh ;
Dureja, Prem ;
Khurana, J. M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) :4089-4099
[3]   Synthesis and characterization of some novel 1,2,4-triazoles, 1,3,4-thiadiazoles and Schiff bases incorporating imidazole moiety as potential antimicrobial agents [J].
Aouad, Mohamed Reda ;
Messali, Mouslim ;
Rezki, Nadjet ;
Ali, Adeeb Al-Sheikh ;
Lesimple, Alain .
ACTA PHARMACEUTICA, 2015, 65 (02) :117-132
[4]   Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity [J].
Badr, Sahar M. I. ;
Barwa, Rasha M. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (15) :4506-4512
[5]   Synthesis and antitumor activity studies of some new fused 1,2,4-triazole derivatives carrying 2,4-dichloro-5-fluorophenyl moiety [J].
Bhat, K. Subrahmanya ;
Poojary, Boja ;
Prasad, D. Jagadeesh ;
Naik, Prashantha ;
Holla, B. Shivarama .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (12) :5066-5070
[6]   Synthesis and anticonvulsant activity of new phenytoin derivatives [J].
Botros, S. ;
Khalil, Nadia A. ;
Naguib, Bassem H. ;
El-Dash, Yara .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 60 :57-63
[7]   Gas-phase pyrolysis of 4-amino-3-allylthio-1,2,4-triazoles:: a new route to [1,3]thiazolo[3,2-b][1,2,4]triazoles [J].
Cartwright, DDJ ;
Clark, BAJ ;
McNab, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (04) :424-428
[8]  
Desai S, 2013, INDIAN J CHEM B, V52, P1176
[9]   A new synthetic access to 2-N-(glycosyl)thiosemicarbazides from 3-N-(glycosyl)oxadiazolinethiones and the regioselectivity of the glycosylation of their oxadiazolinethione precursors [J].
El Ashry, El Sayed H. ;
El Tamany, El Sayed H. ;
Fattah, Mohy El Din Abdel ;
Aly, Mohamed R. E. ;
Boraei, Ahmed T. A. ;
Duerkop, Axel .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :135-146
[10]   Synthesis of New Functionalized 2-Alkylsulfanyl-5-(1H-indol-2-yl)-1,3,4-Oxadiazole and a Facile Thio-Aza-Claisen Rearrangement of the S-Allyl Analog [J].
El Ashry, El Sayed H. ;
El Tamany, El Sayed H. ;
El Fattah, Mohy El Din Abd ;
Aly, Mohamed R. E. ;
Boraei, Ahmed T. A. .
LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (06) :462-469
123