合成路线:This compound can be obtained by two related ways:1) The cyclization of 3-cyclohexylpropionitrile (I) with thiosemicarbazide (II) by means of trifluoroacetic acid gives 5-(2-cyclohexylethyl)-1,3,4-thiadiazol-2-amino (III),which is submitted to a new cyclization process with bis(2,4,6-trichlorophenyl)malonate (IV) in refluxing xylene yielding 2-(2-cyclohexylethyl)-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (V) (1-3).The nitration of (V) with fuming nitric acid in acetic acid affords the corresponding 7-hydroxy-6-nitro derivative (VI),which is treated with POCl3 and tripropylamine to afford the 7-chloro-6-nitro derivative (VII).The reaction of (VII) with concentrated aqueous NH4OH in ethanol gives the corresponding 7-amino-6-nitro compound (VIII),which is reduced with Sn-HCl in dioxane-water to afford the 6,7-diamino derivative (IX).Finally,this compound is dissolved in aqueous HCl and treated with NaNO2.2) The cyclization of 3-cyclohexylpropionic acid (X) with thiosemicarbazide (II) by means of hot H2SO4 gives the thiadiazole (III),which is cyclized again with malonic acid (XI) by means of POCl3 in hot toluene to afford the previously obtained thiadiazolopyrimidine (V).
参考文献标题:Agents for treatment of gastrointestinal diseases
文献作者:Narabayashi,Y.(Daiichi Pharmaceutical Co.,Ltd.)
参考来源:JP 1990138216
合成路线:This compound can be obtained by two related ways:1) The cyclization of 3-cyclohexylpropionitrile (I) with thiosemicarbazide (II) by means of trifluoroacetic acid gives 5-(2-cyclohexylethyl)-1,3,4-thiadiazol-2-amino (III),which is submitted to a new cyclization process with bis(2,4,6-trichlorophenyl)malonate (IV) in refluxing xylene yielding 2-(2-cyclohexylethyl)-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (V) (1-3).The nitration of (V) with fuming nitric acid in acetic acid affords the corresponding 7-hydroxy-6-nitro derivative (VI),which is treated with POCl3 and tripropylamine to afford the 7-chloro-6-nitro derivative (VII).The reaction of (VII) with concentrated aqueous NH4OH in ethanol gives the corresponding 7-amino-6-nitro compound (VIII),which is reduced with Sn-HCl in dioxane-water to afford the 6,7-diamino derivative (IX).Finally,this compound is dissolved in aqueous HCl and treated with NaNO2.2) The cyclization of 3-cyclohexylpropionic acid (X) with thiosemicarbazide (II) by means of hot H2SO4 gives the thiadiazole (III),which is cyclized again with malonic acid (XI) by means of POCl3 in hot toluene to afford the previously obtained thiadiazolopyrimidine (V).
参考文献标题:Antiallergic and antiinflammatory agents
文献作者:Aihara,S.(Daiichi Pharmaceutical Co.,Ltd.)
参考来源:JP 1990138215
合成路线:This compound can be obtained by two related ways:1) The cyclization of 3-cyclohexylpropionitrile (I) with thiosemicarbazide (II) by means of trifluoroacetic acid gives 5-(2-cyclohexylethyl)-1,3,4-thiadiazol-2-amino (III),which is submitted to a new cyclization process with bis(2,4,6-trichlorophenyl)malonate (IV) in refluxing xylene yielding 2-(2-cyclohexylethyl)-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (V) (1-3).The nitration of (V) with fuming nitric acid in acetic acid affords the corresponding 7-hydroxy-6-nitro derivative (VI),which is treated with POCl3 and tripropylamine to afford the 7-chloro-6-nitro derivative (VII).The reaction of (VII) with concentrated aqueous NH4OH in ethanol gives the corresponding 7-amino-6-nitro compound (VIII),which is reduced with Sn-HCl in dioxane-water to afford the 6,7-diamino derivative (IX).Finally,this compound is dissolved in aqueous HCl and treated with NaNO2.2) The cyclization of 3-cyclohexylpropionic acid (X) with thiosemicarbazide (II) by means of hot H2SO4 gives the thiadiazole (III),which is cyclized again with malonic acid (XI) by means of POCl3 in hot toluene to afford the previously obtained thiadiazolopyrimidine (V).
参考文献标题:Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives.II.6-Alkyl- and 6-cycloalkylalkyl derivatives
文献作者:Miwa,T.; Fujiwara,H.; Mori,M.; Moroi,R.; Aibara,S.; Iwamoto,T.; Tsukada,W.; Nakayama,K.; Matsumoto,H.; Yokohama,S.; et al.
参考来源:Chem Pharm Bull 1992,40(9),2391-8
合成路线:This compound can be obtained by two related ways:1) The cyclization of 3-cyclohexylpropionitrile (I) with thiosemicarbazide (II) by means of trifluoroacetic acid gives 5-(2-cyclohexylethyl)-1,3,4-thiadiazol-2-amino (III),which is submitted to a new cyclization process with bis(2,4,6-trichlorophenyl)malonate (IV) in refluxing xylene yielding 2-(2-cyclohexylethyl)-7-hydroxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (V) (1-3).The nitration of (V) with fuming nitric acid in acetic acid affords the corresponding 7-hydroxy-6-nitro derivative (VI),which is treated with POCl3 and tripropylamine to afford the 7-chloro-6-nitro derivative (VII).The reaction of (VII) with concentrated aqueous NH4OH in ethanol gives the corresponding 7-amino-6-nitro compound (VIII),which is reduced with Sn-HCl in dioxane-water to afford the 6,7-diamino derivative (IX).Finally,this compound is dissolved in aqueous HCl and treated with NaNO2.2) The cyclization of 3-cyclohexylpropionic acid (X) with thiosemicarbazide (II) by means of hot H2SO4 gives the thiadiazole (III),which is cyclized again with malonic acid (XI) by means of POCl3 in hot toluene to afford the previously obtained thiadiazolopyrimidine (V).
参考文献标题:DS-4574
文献作者:Rabasseda,X.; Castar,J.; Mealy,N.
参考来源:Drugs Fut 1994,19(10),901
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