Regioselective synthesis of novel 4-aryl-2-ethylthio-7-methyl pyrazolo[1,5-a]-[1,3,5]-triazines

Hydrogen-bonding patterns in two aroylthiocarbamates and two aroylimidothiocarbonates

“…O,S-Dialkyl aroylimidothiocarbonates are structural analogues of S,S-dialkyl aroylimidothiocarbonates, which have been widely used as synthetic starting materials (Augustín et al, 1980;Sato et al, 1981;Fukada et al, 1985Fukada et al, , 1986Fukada et al, , 1990Insuasty et al, 2006Insuasty et al, , 2008. We report here the structures of two O-ethyl aroylthiocarbamates, (I) and (II) (Figs.…”

Anion-tuning of supramolecular gel properties

“…The reaction of tbutyl isothiocyanate with 3-amino-5-methylpyrazole in refluxing CHCl 3 was performed, and, in agreement with literature results, the derived thiourea compound 3.3 was isolated. 7,48,[53][54][55] The reaction of isocyanates with 3-amino-5-methylpyrazole resulted in the formation of carboxamides, compounds 3.1 and 3.2, for example. 7,47,48 This problem was circumvented by BOC-protection of the pyrazole ring allowing for the urea functionalisation of the amine group to yield the desired urea functionalised pyrazole compounds.…”

“…isothiocyanates reported in the literature all appear to produce a thiourea except in one case. 7,48,[53][54][55] In this one case, where carbothioamides were produced, the reactions were performed at room temperature in acetone whereas in the other examples the reactions were performed in a refluxing solvent. 54 This result shows that the temperature and solvent of the reaction play important roles in determining the product of the reaction between a thioisocyanate and an aminopyrazole.…”

“…55 The gelation ability of the compounds was assessed by dissolving the compounds at 1% by weight in a variety of solvents, namely MeCN, CHCl 3 , MeOH, EtOH and solvent mixtures such as DMSO/H 2 O and MeOH/H 2 O (Table 2.2). The compounds 2.1e (n = 6) and 2.1g (n = 8) gelled CHCl 3 to form completely thermally reversible transparent gels at 1% weight and the compounds with 2.1a (n = 2) and 2.1c (n = 4) readily formed semi-transparent thermally reversible organogels in MeCN and CHCl 3 after slow cooling from the hot solutions.…”

A new and convenient synthesis of 2-arylbenzimidazoles through reaction of benzoylisothiocyanates with ortho-phenylenediamines

“…19 The reactions of benzoylisothiocyanates are of interest to organic chemists from synthetic and mechanistic point of view. 20 The reactions of these heterocumulenes often depend on the structure of the isothiocyanates. 21 In the present paper, we report 2:1 molar reactions of bezoylisothiocyanates with 1,2-phenylenediamines resulting into formation of corresponding bisthioureas which undergo cyclization to 2-arylbenzimidazoles by refluxing in pyridine.…”