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1.
Chia-Yang Shiau Ji-Wang Chern Jung-Hsiung Tien Kang-Chien Liu 《Journal of heterocyclic chemistry》1989,26(3):595-596
2-(2-Chloroethylureido)- and 2-(3-chloropropylureido)thiobenzamides 5a, b were prepared in good yields by treating 2-aminothiobenzamide with 2-chloroethyl and 3-chloropropyl isocyanates respectively. Subsequent treatment of compound 5a and 5b either with alkali or mineral acid led to the formation of 2, 3-dihydro-imidazo[1, 2-c]quinazolin-5(6H)-one 7a and 3, 4-Dihydro-2H-pyrimido[1, 2-c]quinazolin-6(7H)-one 7b . 相似文献
2.
L. G. Payne J. Przytycki A. A. Patchett M. T. Wu 《Journal of heterocyclic chemistry》1979,16(2):391-391
2,3-Dihydro-5H-thiazolo[2,3-b]quinazolin-5-one and 3,4-dihydro-2H,6H[1,3] thiazino[2,3-b]-quinazolin-6-one have been synthesized in one step by the reaction of methyl anthranilate with ehloroalkyl isothiocyanates. 相似文献
3.
V. M. Kisel L. M. Potikha A. V. Turov V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2001,37(9):1153-1161
Borohydride reduction in a series of 7-benzyl- and newly synthesized 7-arylmethylene-7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones leads stereoselectively to erythro-7-benzyl-6,6a,7,12-tetrahydro-5H-isoquino[2,3-a]quinazolin-5-ones. 7,7-Disubstituted 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones are inert to the action of sodium borohydride, but spiro[5H-isoquino[2,3-a]quinazolin-7(12H),2'-indane]-5-one is reduced under rigid conditions to 6,6a-dihydrospiro[5H-isoquino[2,3-a]quinazolin-7(12H),2'-indan]-5-one. 7-Acetyl- and 7-benzoyl-6,11-dihydro-5H-isoquino[2,3-a]quinazolin-5-ones are converted in an aqueous alcoholic solution of sodium borohydride to the previously described 6,6a,7,12-tetrahydro-5H-isoquino[2,3-a]quinazolin-5-one. The structure and special features of the conformational behavior of the reduction products obtained were demonstrated by 1H NMR spectroscopy.! 相似文献
4.
Andrea Santagati Maria Santagati Filippo Russo Giuseppe Ronsisvalle 《Journal of heterocyclic chemistry》1988,25(3):949-953
Continuing earlier studies designed to obtain derivatives of 1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one and of the isomeric 7-one of pharmacological interest, some novel compounds 2 and derivatives of 6,7,8,9-tetrahydro-5H-1,3,4-thiadiazolo[2,3-b]quinazolin-5-one ( 3 ) were prepared. Derivatives of pyrimido[2,1-b]benzothiazol-2-one ( 6 ) and of the isomeric 4-one derivatives 8 were also synthesized. Structural identification was obtained by 1H-nmr, ir and mass spectra. 相似文献
5.
Chia-Yang Shiau Ji-Wang Chern Kang-Chien Liu Chao-Han Chan Mou-Hsiung Yen Ming-Chu Cheng Yu Wang 《Journal of heterocyclic chemistry》1990,27(5):1467-1472
To search for novel antihypertensive heterocycles in the condensed quinazoline series, two representative compounds were synthesized via a suitable reaction sequences. Treating anthranilonitrile with allyl isocyanate gave 2-(allylureido)benzonitrile ( 10 ) in a quantitative yield. Compound 10 was cyclized to 3-allylquinazoline-2(1H, 4(3H)-dione ( 11 ). Bromination of 11 in carbon tetrachloride converted it into the corresponding 3-(2,3-dibromopropyl) derivative ( 12 ) in 92% yield. Ring closure of 12 was effected by the action of alkali to afford 2-bromomethyl-2,3-dihydro-5H-oxazolo[2,3-b]quinazolin-5-one ( 13 ). The title compound, 2-(4-benzylpiperazin-1-ylmethyl)-2,3-dihydro-5H-oxazolo[2,3-b]quinazolin-5-one ( 7 ) could be obtained by a reaction of either 12 or 13 with 1-benzylpiperazine respectively. Starting from the readily available 3-allyl-2H-thioxoquinazolin-4(3H)-one ( 16 ) via the analogous reactions gave the 2-bromomethyl-2,3-dihydro-5H-thiazolo[2,3-b]-quinazolin-5-one ( 19 ) in good yield. However, the reaction of 19 with 1-benzylpiperazine provided another target compound, 2-(4-benzylpiperazin-1-ylmethyl)-2,3-dihydro-5H-thiazolo[2,3-b]quinazolin-5-one ( 8 ) only in poor yield (8%). As major product, the dehydrobrominated compound, 2-methylene-2,3-dihydro-5H-thiazolo[2,3-b]quinazolin-5-one ( 22 ) was isolated. A preliminary pharmacological evaluation revealed that both compounds 7 and 8 are devoid of the antihypertensive activity. 相似文献
6.
Isatoic anhydride ( 1a ) and 5-chloroisatoic anhydride ( 1b ) were treated with 2-(1-methylhydrazino)ethanol ( 2 ) to produce 2-aminobenzoic acid 2-(2-hydroxyethyl)-2-methylhydrazide ( 3a ) and its 5-chloro analog 3b , respectively. Treatment of 3a and 3b with carbon disulfide gave, respectively, 2,3-dihydro-3-[(2-hydroxyethyl)methylamino]-2-thioxo-4-(1H)quinazolinone ( 4a ) and its 6-chloro analog 4b . Compounds 4a and 4b afforded 5,6-dihydro-5-methyl-2-thioxo-4H,8H-[1,3,5,6]oxathiadiazocino[4,5-b]quinazolin-8-one ( 5a ) and its 10-chloro analog 5b , respectively, upon treatment with thiophosgene. Compound 5a could be produced directly from 3a and thiophosgene. Treatment of 4a and 4b with trifluoroacetic anhydride followed by potassium carbonate gave 3,4-dihydro-4-methyl-2H,6H-[1,3,4]thiadiazino[2,3-b]quinazolin-6-one ( 7a ) and its 8-chloro analog 7b , respectively. Treatment of 4a with thionyl chloride also gave 7a , but 4b and thionyl chloride afforded a mixture of 7b and 8-chloro-3,4-dihydro-4-methyl-2H,6H-[1,3,4]oxadiazino[2,3-b]quinazolin-6-one ( 10 ). The dimethyl analogs of 4a and 4b ( 13a and 13b ) upon treatment with thiophosgene afforded 3,4-dihydro-2,2,4-trimethyl-2H,6H-[1,3,4]oxadiazino[2,3-b]quinazolin-6-one ( 14a ) and its 8-chloro analog 14b , respectively. 相似文献
7.
Eleftherios Paul Papadopoulos 《Journal of heterocyclic chemistry》1980,17(7):1553-1558
The reaction of anthranilonitrile with 2-chloroethyl isocyanate yields 2-[3-(2-chloroethyl)ureido]benzo-nitrile ( 6 ) which, upon heating, or treatment with base, undergoes a double cyclization to form 2,6-dihydroimidazo[1,2-c]quinazolin-5-(3H) one ( 8 ) in excellent yield. When heated with hydrochloric acid, 6 is converted initially into 2-(2-chloroethylamino)-4H-[3,1]benzoxazin-4-one ( 18 ) and further into 3-(2-chloroethyl)-2,4-(1H,3H)quinazolinedione ( 15 ). The acid-catalyzed reaction of 2,3-dihydro-5H-oxazolo[2,3-b]quinazolin-5-one ( 14 ) with nucleophilic reagents yields 3-substituted 2,4-(1H,3H)quinazolinediones. 相似文献
8.
Milo Budínský Jindich Symerský Jaroslav Podlaha Jana Podlahov Zdenk Polívka Miroslav Protiva 《Journal of heterocyclic chemistry》1989,26(5):1229-1235
The unexpected formation of 11H-pyrido[2,1-b]quinazolin-11-one derivative 6 from 5,11-dihydro-6H-pyrido[2,3-b]-1,4-benzodiazepin-6-one (2) has been observed. Its structure 6 was determined by X-ray crystallography. Detailed nmr study provided a complete set of proton and carbon-13 nmr parameters of compound 6 in solution. 相似文献
9.
A convenient and sustainable synthesis of pyrazolo[1,5-a]quinazolin-5(4H)-ones and [1,2,4]triazolo[1,5-a]quinazolin-5(4H)-one through copper-catalyzed cascade reactions of 2-bromobenzoates with 1H-pyrazol-5-amines or 1H-1,2,4-triazol-5-amine under ligand-free conditions in water is presented. It is notable that aqueous medium turned out to be crucial for the chemoselective formation of the title compounds. Compared with literature protocols, this new method showed advantages such as simple and sustainable procedure, commercially available starting materials, and convenient reuse of the reaction medium together with the copper catalyst. 相似文献
10.
Heating 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one with isonicotinoyl chloride in pyridine gives 6-isonicotinoyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one. The 1-alkyl-4[(11-oxo-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-6-yl)carbonyl]pyridinium iodides obtained by alkylation of 6-isonicotinoyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one using alkyl iodides in the presence of NaH are converted to 1′-R-spiro[7H,8H-2a,7a-diazacyclopenta[fg]naphthacene-2,4′(1′H)-pyridine]-1,8(2H)-diones. The chemical and spectroscopic properties of the spiro compounds obtained
were studied.
For Communication 32 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 52–58, January, 2009. 相似文献
11.
Istvn Hermecz Ildik Szilgyi Lszl Orfi Jzsef Kksi Gyrgy Szsz 《Journal of heterocyclic chemistry》1993,30(5):1413-1420
3,4-Dihydro-1H,6H-[1,4]oxazino[3,4-b]quinazolin-6-one 3 and its 1-methyl and 1-hydroxy derivatives 8 and 13 were prepared by different routes. The active methylene group of compound 3 was reacted with electro-hilic reagents (bromine, phenyldiazonium chloride, nitrous acid, a Vielsmeier-Haack reagent, aromatic aldehydes and diethyl oxalate) to yield 1-substituted-3,4-dihydro[1H,6H)-1,4-oxazino[3,4-b]quinazo-lin-6-ones. The reactivity of 1-hydroxy and 1-bromo derivatives 13 and 15 were also investigated in some reactions. The 3,4-dihydro-lH,6H-[1,4]oxazino[3,4-b]quinazolin-6-ones were characterized by means of uv, 1H and 13C nmr spectroscopy. 相似文献
12.
Ji-Wang Chern Fang-Jy Shish Chau-Dung Chang Chao-Han Chan Kang-Chien Liu 《Journal of heterocyclic chemistry》1988,25(4):1103-1105
2,3-Dihydro-5H-oxazolo[2,3-b]quinazolin-5-one 5a was synthesized from anthranilamide 1 and 2-chloro-ethyl isocyanate either by a direct reflux in methanol, or by stirring at room temperature in acetonitrile leading to the intermediate, 2-(2-chloroethyl ureido)benzamide 6a which was subsequently cyclized on heating with an organic base. However, when compound 6a was refluxed with concentrated hydrochloric acid, it furnished 3-(2-chloroethyl)-2,4-dioxo-1H,3H-quinazoline 2a in good yields. 3,4-Dihydro-2H,6.H-[1,3]-oxazino[2,3-b]quinazolin-6-one 5b , 3-(3-chloropropyl)-2,4-dioxo-1H,3.H-quinazoline 2b and 2-(3-chloropropyl ureido)benzamide 6b were obtained similarly from 1 and 3-chloropropyl isocyanate. 相似文献
13.
G. N. Lipunova E. V. Nosova A. A. Laeva M. I. Kodess V. N. Charushin 《Russian Journal of Organic Chemistry》2005,41(7):1071-1080
Methods for the synthesis of fluorine-containing derivatives of 2-imino-1,3-diphenylquinazolin-4-one, imidazo[1,2-a]quinazolin-5-one, pyrazolo[1,5-a]quinazolin-5-one, and [1,2,4]triazolo[1,5-a]quinazolin-5-one were developed on the basis of the reaction of tetrafluorobenzoyl chloride with N,N′-diphenylguanidine and aminoazoles.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 1092–1100.Original Russian Text Copyright © 2005 by Lipunova, Nosova, Laeva, Kodess, Charushin. 相似文献
14.
Iodide-catalyzed ring expansion of 2-[(1-aziridinylcarbonyl)amino]benzoic acid methyl ester (2) gave 2,3-dihydro-5H-oxazolo[2,3-b]quinazolin-5-one (3) in quantitative yield. Treatment of the dimethyl analog of 2 (9) with sodium iodide in acetone gave a mixture of the 2,3-dihydro-2,2-dimethyl- (10) and 2,3-dihydro-3,3-dimethyl-5H-oxazolo[2,3-b]quinazolin-5-ones (11). However, rearrangement of 9 with sulfuric acid produced only 10. Synthesis of 11 by another route for comparison is described, and the known syntheses of 2,3-dihydro-5H-oxazolo[2,3-b]quinazolin-5-ones are reviewed. 相似文献
15.
Somepalli Venkateswarlu Meka Satyanarayana Gandrothu Narasimha Murthy Vidavalur Siddaiah 《Tetrahedron letters》2012,53(21):2643-2646
Cyclisation of 2-(2-aminophenyl)quinazolin-4(3H)-ones on to N3 and on to N1 leading to 6-alkyl-(8H)-quinazolino[4,3-b]quinazolin-8-one and 6-alkyl-(13H)-quinazolino[3,4-a]quinazolin-13-one, respectively was described for the first time. The differences in the IR and carbon NMR data of these isomeric fused quinazolinoquinazolinones afford a useful method for distinguishing between the two series. 相似文献
16.
Henri Stalder 《Helvetica chimica acta》1986,69(8):1887-1897
Metabolites of 1,5-Dihydroimidazo[2,1-b ]quinazolin-2(3H)-ones. Preparation and Reactions of Some 1,5-Dihydro-3-hydroxyimidazo[2,1-b]quinazolin-2(3H)-ones Hydroxylated 1,5-dihydroimidazo[2,1-b]quinazolin-2(3H)-ones 2–4 and 6 were isolated as metabolites of imidazoquinazolinones 1a and 1b , respectively. The synthesis of 1,5-dihydro-3-hydroxy-3-methylimidazo[2,1-b]quinazolin-2(3H)-ones 3 , 4 , and 6 , and the preparation of some derivatives thereof is described. 相似文献
17.
Three-component condensation of 3(5)-aminoazoles with benzaldehydes and dimedone in acetonitrile in the presence of montmorillonite KSF as heterogeneous catalyst regioselectively afforded 5,6,7,9-tetrahydroazolo[5,1-b]quinazolin-8(4H)-one derivatives in good yields. Oxidation of the condensation products with ceric ammonium nitrate in acetone gave the corresponding 6,7-dihydroazolo[5,1-b]quinazolin-8(5H)-ones. 相似文献
18.
François-René Alexandre Amaya BerecibarRoger Wrigglesworth Thierry Besson 《Tetrahedron letters》2003,44(24):4455-4458
An original route to the rare 8H-thiazolo[5,4-f]quinazolin-9-one 1 and the novel 7H-thiazolo[4,5-h]quinazolin-6-one 2 is described. Access to the regioisomers was realized by fusion of a thiazole and a quinazoline ring via Appel's salt chemistry. Thermal reactions were carried out using a focused microwave reactor, reducing the overall time of the multi-step synthesis. 相似文献
19.
The synthesis of pyrazino[2,3-g]quinazolin-2,4-(1H,3H)dione ( 4 ) and its 7,8-dimethyl derivative ( 5 ), as linear benzo-separated lumazines, is reported. Also described is the preparation of 2-amino-6,7,8,9-tetrahydro-7,8-dimethylpyrazino[2,3-g]quinazolin-4-one ( 6 ), as a linear benzo-separated analog of a synthetic cofactor for phenylalanine hydroxylase. All of the syntheses began with ethyl 2,4,5-triaminobenzoate ( 8 ) and proceeded through the appropriate derivatives of ethyl 6-aminoquinoxaline-7-carboxylate ( 9, 10 , and 11 ) which were subsequently ring closed to 4, 5 , and 6 . 相似文献
20.
The reaction of epibromohydrin with hydroxyquinazolin-2-(1H)one derivatives. Novel oxazine formation
Mary Lou Cotter Victor Bandurco Elizabeth Wong Zoltan G. Hajos 《Journal of heterocyclic chemistry》1979,16(3):623-624
Epibromohydrin was found to react with 7-hydroxy-2-methylpyrrolo[1,2-c]quinazolin-5(6H)-one ( 4 ) in the presence of sodium hydroxide to form the novel oxazine 5 . The structure of compound 5 was proven by cmr and pmr analysis. 相似文献