Facile synthesis of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-onesviaa sequential Ugi–Smiles type/nucleophilic substitution/cyclization reaction

2018 ◽  
Vol 42 (21) ◽  
pp. 17533-17537
Author(s):  
Sorour Ramezanpour ◽  
Mohammad Nasim Rezaei ◽  
Aref Vaezghaemi ◽  
Frank Rominger

An innovative strategy for synthesis of a library of complex multi-substituted 1,2,4-triazine-6-ones. These structures are analogues of pyrimidine bases with possible enhanced biological activities.

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 530-537 ◽  
Author(s):  
Moisés Romero-Ortega ◽  
Michelle Trujillo-Lagunas ◽  
Ignacio Medina-Mercado ◽  
Ivann Zaragoza-Galicia ◽  
Horacio Olivo

A convenient two-step, one-pot synthesis of 4-chloro-2-(trichloromethyl)pyrimidines starting from 2-(trichloromethyl)-1,3-diazabutadienes is described. These nitrogen heterocycles were prepared by a sequential acylation/intramolecular cyclization reaction between 2-(trichloromethyl)-1,3-diazabutadienes and acyl chlorides in the presence of triethylamine followed by treatment with POCl3. This is the first report for the synthesis of this type of 4-chloro-2-(trichloromethyl)pyrimidine derivatives and serves as a source for a wide variety of other substituted pyrimidines by nucleophilic substitution reactions.


Synlett ◽  
2019 ◽  
Vol 30 (09) ◽  
pp. 1053-1056 ◽  
Author(s):  
Jun Xiong ◽  
Qing Min ◽  
Gang Yao ◽  
Jia-An Zhang ◽  
Hai-Feng Yu ◽  
...  

A new facile synthesis of 3,4-dihydroquinazoline-2(1H)-thiones by an Ugi-azide/Staudinger/aza-Wittig/cyclization sequence has been developed. The Ugi-azide reactions of 2-azidobenzaldehydes, amines, trimethylsilyl azide, and isocyanides produced tetrazoles, which, when treated with methyldiphenylphosphane and CS2, produced 3,4-dihydroquinazoline-2(1H)-thiones in good overall yields via a sequential Staudinger/aza-Wittig/cyclization reaction.


2018 ◽  
Vol 16 (21) ◽  
pp. 4013-4020 ◽  
Author(s):  
Akinari Sumita ◽  
Jinhee Lee ◽  
Yuko Otani ◽  
Tomohiko Ohwada

We present a one-pot two-step methodology, in which an unprotected amino is tolerated, for rapidly synthesizing 2,3-benzodiazepines via phosphate-assisted acylation reaction and hydrazine cyclization reaction.


2019 ◽  
Vol 4 (3) ◽  
pp. 152-158
Author(s):  
P.C. Burde ◽  
A.M. Rahatgaonkar

3-Cyclopropyl-5-(4-substituted)-1-phenyl-4,5-dihydro-1H-pyrazoles derived from corresponding chalcones were synthesized and evaluated for their biological activities. A convenient synthesis of a library of these compounds in 1-butyl-3-methylimidazolium hexafluorophosphate-water biphasic system at ambient temperature has been accomplished. The ionic liquid, [bmim][PF6] and water which are immiscible, has been easily recycled and reused after separation of the products without any noticeable diminution in its activity.


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