The title compound 3-benzyl-5-cyclohexylamino-6-phenyl-3,6-dihydro-1,2,3- triazolo[4,5-d]pyrimidin-7-one (C23H24N6O, Mr = 400.48) has been synthesized by means of tandem aza-Wittig reaction, and its crystal structur...The title compound 3-benzyl-5-cyclohexylamino-6-phenyl-3,6-dihydro-1,2,3- triazolo[4,5-d]pyrimidin-7-one (C23H24N6O, Mr = 400.48) has been synthesized by means of tandem aza-Wittig reaction, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 6.5550(6), b = 10.3711(10), c = 31.265(3) ?, β = 93.827(2)o,V = 2120.8(4) ?3, Z = 4, Dc = 1.254 g/cm3, S = 1.025, μ(MoKa) = 0.081 mm-1, F(000) = 848, R = 0.0576 and wR = 0.1368. X-ray analysis reveals that all ring atoms in the triazolopyrimidinone moiety are almost coplanar and the cyclohexyl ring adopts a chair confor- mation.展开更多
Some new 2-aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-ones have been prepared through cyclocondensation of 2-amino 1H-pyrrole-3-carboxamides with aromatic aldehydes followed by air oxidation in the presence of 3-me...Some new 2-aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-ones have been prepared through cyclocondensation of 2-amino 1H-pyrrole-3-carboxamides with aromatic aldehydes followed by air oxidation in the presence of 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate[(CH;);SO;HMIM][HSO;],a Br(?)nsted-acidic ionic liquid,as a green and reusable catalyst in solvent-free conditions.展开更多
The crystal structure of the title compound 1-(4-fluorophenyl) -2-hexylthio-benzo [4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H) -one(C23H21FN4O2S,Mr = 436.5) has been prepared and determined by single-cr...The crystal structure of the title compound 1-(4-fluorophenyl) -2-hexylthio-benzo [4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H) -one(C23H21FN4O2S,Mr = 436.5) has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic,space group P21/n with a = 13.9854(3) ,b = 17.2678(4) ,c = 18.1828(5)A,β = 99.364(2) °,V = 4332.58(18) A^3,Z = 4,Dc = 1.338,F(000) =1824,μ = 0.185 mm^-1,MoKa radiation(λ = 0.71073) ,R = 0.0538 and wR = 0.1162 for 4728 observed reflections with I 〉 2σ(I) . X-ray diffraction analysis reveals the fused rings of benzo[4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a] pyrimidin-5(1H) -one system are nearly coplanar. The crystal packing is mainly stabilized by weak intermolecular C-H···O hydrogen bond and π-π interactions.展开更多
A series of novel pyrazolo [ 4,3-d ] pyrimidin-7-ones was designed and synthesized in order to find new potent phosphodiesterase 5 inhibitors(PDE5). The structures of all the compounds were confirmed by IR, ^1H NMR ...A series of novel pyrazolo [ 4,3-d ] pyrimidin-7-ones was designed and synthesized in order to find new potent phosphodiesterase 5 inhibitors(PDE5). The structures of all the compounds were confirmed by IR, ^1H NMR and MS; their in vitro vasodilatory activities were tested on isolated rabbit aortic spiral strips. Among them, compound X3 displays a significant vasodilatory activity, which is more potent than verapamil.展开更多
A rapid and efficient method for the synthesis of isoxazolo[5,4-d]pyrimidin-4(5H)-ones has been developed through cyclocondensation of 5-aminoisoxazole-4-carboxamides with orthoesters under conventional heating and ...A rapid and efficient method for the synthesis of isoxazolo[5,4-d]pyrimidin-4(5H)-ones has been developed through cyclocondensation of 5-aminoisoxazole-4-carboxamides with orthoesters under conventional heating and solvent-free microwave irradiation with solid acid catalysis. In comparison, the reactions are faster and the yields are higher under microwave irradiation.展开更多
Twelve novel pyrazolo [4,3-d] pyrimidin-7-ones were synthesized and their structures were confirmed by IR, 1H NMR and MS. Their in vitro bronchodilatory activities were tested in guinea-pigs. The pharmacological res...Twelve novel pyrazolo [4,3-d] pyrimidin-7-ones were synthesized and their structures were confirmed by IR, 1H NMR and MS. Their in vitro bronchodilatory activities were tested in guinea-pigs. The pharmacological results show that compound 11c has more potent activity than aminophylline.展开更多
The crystal structure of the new title compound 2-ethoxy-3-n-butyl- benzofuro[2,3d]pyrimidin-4(3H)-one (C16H18N2O3, Mr = 286.32) has been prepared and determined by singlecrystal X-ray diffraction. The crystal is ...The crystal structure of the new title compound 2-ethoxy-3-n-butyl- benzofuro[2,3d]pyrimidin-4(3H)-one (C16H18N2O3, Mr = 286.32) has been prepared and determined by singlecrystal X-ray diffraction. The crystal is of monoclinic, space group P21/c with a = 13.7167(14), b = 13.113(1), c = 8.378(1) A, β = 98.992(2)^o, V = 1488.4(3) A^3, Z = 4, Dc = 1.278, F(000) = 608, μ = 0.089 mm^-1, MoKa radiation (2 = 0.71073), R = 0.0498, wR = 0.1238 for 2336 observed reflections with I 〉 2σ(I). X-ray diffraction analysis reveals that all ring atoms in the benzo[4, 5]furo [2,3-d] pyrimi- dinone moieties are almost coplanar.展开更多
5-Substituted 7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones (4) were rapidly prepared by a solution-phase parallel synthetic method, which includes aza-Wittig reaction of iminophosphorane (1) with phenyl isocynate to g...5-Substituted 7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones (4) were rapidly prepared by a solution-phase parallel synthetic method, which includes aza-Wittig reaction of iminophosphorane (1) with phenyl isocynate to give car- bodiimide (2) and subsequent reaction of 2 with various amine and alcohols in the presence of catalytic amount of sodium alkoxide in a parallel fashion.展开更多
A new efficient synthesis of 2,5,6-trisubstituted oxazolo(5,4-d]pyrimidi-7(6H)-ones by consecutive azaWittig reaction was developed.The sequential three-component reaction of oxazolyliminophosphorane4,isocyanates a...A new efficient synthesis of 2,5,6-trisubstituted oxazolo(5,4-d]pyrimidi-7(6H)-ones by consecutive azaWittig reaction was developed.The sequential three-component reaction of oxazolyliminophosphorane4,isocyanates and amines produced 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones 7 in good overall yields in the presence of catalytic amount of EtONa.展开更多
An efficient method for the synthesis of novel pyrido[3'',2'':4',5']thieno[3',2':2,3]pyrido [4,5:d][1,3]thiazolo[3,2-a]pyrimidine-4-one derivatives(5) has been developed using a Pictet–Spengler reaction ...An efficient method for the synthesis of novel pyrido[3'',2'':4',5']thieno[3',2':2,3]pyrido [4,5:d][1,3]thiazolo[3,2-a]pyrimidine-4-one derivatives(5) has been developed using a Pictet–Spengler reaction between 2-(3-aminothieno[2,3-b]pyridin-2-yl)thiazolo[3,2-a] pyrimidin-5-one(3), which could be obtained from the condensation of 7-(chloromethyl)-5H-thiazolo[3,2-a]pyrimidin-5-one(1) with3-cyanopyridine-2-thione(2) via Thorpe–Ziegler isomerization, and aromatic aldehydes under NH2SO3 H as catalysis in good yields.展开更多
基金The project was supported by the National Key Project for Basic Research (2003CB114400 2003CB114406) and National Natural Science Foundation of China (20102001)
文摘The title compound 3-benzyl-5-cyclohexylamino-6-phenyl-3,6-dihydro-1,2,3- triazolo[4,5-d]pyrimidin-7-one (C23H24N6O, Mr = 400.48) has been synthesized by means of tandem aza-Wittig reaction, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 6.5550(6), b = 10.3711(10), c = 31.265(3) ?, β = 93.827(2)o,V = 2120.8(4) ?3, Z = 4, Dc = 1.254 g/cm3, S = 1.025, μ(MoKa) = 0.081 mm-1, F(000) = 848, R = 0.0576 and wR = 0.1368. X-ray analysis reveals that all ring atoms in the triazolopyrimidinone moiety are almost coplanar and the cyclohexyl ring adopts a chair confor- mation.
文摘Some new 2-aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-ones have been prepared through cyclocondensation of 2-amino 1H-pyrrole-3-carboxamides with aromatic aldehydes followed by air oxidation in the presence of 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate[(CH;);SO;HMIM][HSO;],a Br(?)nsted-acidic ionic liquid,as a green and reusable catalyst in solvent-free conditions.
基金Supported by the Natural Science Foundation of Hubei Province (2006ABB016)Key Science Research Project of Hubei Provincial Department of Education (No.D200724001)the Science Research Project of Yunyang Medical College (No.2008CXG01)
文摘The crystal structure of the title compound 1-(4-fluorophenyl) -2-hexylthio-benzo [4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H) -one(C23H21FN4O2S,Mr = 436.5) has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic,space group P21/n with a = 13.9854(3) ,b = 17.2678(4) ,c = 18.1828(5)A,β = 99.364(2) °,V = 4332.58(18) A^3,Z = 4,Dc = 1.338,F(000) =1824,μ = 0.185 mm^-1,MoKa radiation(λ = 0.71073) ,R = 0.0538 and wR = 0.1162 for 4728 observed reflections with I 〉 2σ(I) . X-ray diffraction analysis reveals the fused rings of benzo[4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a] pyrimidin-5(1H) -one system are nearly coplanar. The crystal packing is mainly stabilized by weak intermolecular C-H···O hydrogen bond and π-π interactions.
基金Supported by the Natural Science Foundation of Liaoning Province(No. 20032043)
文摘A series of novel pyrazolo [ 4,3-d ] pyrimidin-7-ones was designed and synthesized in order to find new potent phosphodiesterase 5 inhibitors(PDE5). The structures of all the compounds were confirmed by IR, ^1H NMR and MS; their in vitro vasodilatory activities were tested on isolated rabbit aortic spiral strips. Among them, compound X3 displays a significant vasodilatory activity, which is more potent than verapamil.
文摘A rapid and efficient method for the synthesis of isoxazolo[5,4-d]pyrimidin-4(5H)-ones has been developed through cyclocondensation of 5-aminoisoxazole-4-carboxamides with orthoesters under conventional heating and solvent-free microwave irradiation with solid acid catalysis. In comparison, the reactions are faster and the yields are higher under microwave irradiation.
文摘Twelve novel pyrazolo [4,3-d] pyrimidin-7-ones were synthesized and their structures were confirmed by IR, 1H NMR and MS. Their in vitro bronchodilatory activities were tested in guinea-pigs. The pharmacological results show that compound 11c has more potent activity than aminophylline.
基金This work was supported by the Natural Science Foundation of Hubei Province (2006ABB016)National Natural Science Foundation of China (20672041) Key Project of Science and Technology of Ministry of Education of China (107082, 106116)
文摘The crystal structure of the new title compound 2-ethoxy-3-n-butyl- benzofuro[2,3d]pyrimidin-4(3H)-one (C16H18N2O3, Mr = 286.32) has been prepared and determined by singlecrystal X-ray diffraction. The crystal is of monoclinic, space group P21/c with a = 13.7167(14), b = 13.113(1), c = 8.378(1) A, β = 98.992(2)^o, V = 1488.4(3) A^3, Z = 4, Dc = 1.278, F(000) = 608, μ = 0.089 mm^-1, MoKa radiation (2 = 0.71073), R = 0.0498, wR = 0.1238 for 2336 observed reflections with I 〉 2σ(I). X-ray diffraction analysis reveals that all ring atoms in the benzo[4, 5]furo [2,3-d] pyrimi- dinone moieties are almost coplanar.
文摘5-Substituted 7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones (4) were rapidly prepared by a solution-phase parallel synthetic method, which includes aza-Wittig reaction of iminophosphorane (1) with phenyl isocynate to give car- bodiimide (2) and subsequent reaction of 2 with various amine and alcohols in the presence of catalytic amount of sodium alkoxide in a parallel fashion.
基金financial support of this work by the National Natural Science Foundation of China(No.21172085)the Natural Science Foundation of Hubei Province(No. 2014CFB567)the Open Foundation of Hubei Province Key Laboratory of Purification and Application of Plant Anti-cancer Active Ingredients
文摘A new efficient synthesis of 2,5,6-trisubstituted oxazolo(5,4-d]pyrimidi-7(6H)-ones by consecutive azaWittig reaction was developed.The sequential three-component reaction of oxazolyliminophosphorane4,isocyanates and amines produced 2,5,6-trisubstituted oxazolo[5,4-d]pyrimidi-7(6H)-ones 7 in good overall yields in the presence of catalytic amount of EtONa.
文摘An efficient method for the synthesis of novel pyrido[3'',2'':4',5']thieno[3',2':2,3]pyrido [4,5:d][1,3]thiazolo[3,2-a]pyrimidine-4-one derivatives(5) has been developed using a Pictet–Spengler reaction between 2-(3-aminothieno[2,3-b]pyridin-2-yl)thiazolo[3,2-a] pyrimidin-5-one(3), which could be obtained from the condensation of 7-(chloromethyl)-5H-thiazolo[3,2-a]pyrimidin-5-one(1) with3-cyanopyridine-2-thione(2) via Thorpe–Ziegler isomerization, and aromatic aldehydes under NH2SO3 H as catalysis in good yields.