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1.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2006,42(5):693-697
3-Amino-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-ones were converted into 2-aryl-5H-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-ones
on treatment with carboxylic acids and POCl3. 3-Arylmethylidenamino-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-ones also cyclized to 2-aryl-5H-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-ones
when oxidized with potassium chlorate in acetic acid, but on heating they were deaminated to give 2-thioxo-1,2,3,4-tetrahydroquinazolin-4-one
and aryl nitriles.
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Translated from Khimiya Geteotsiklicheskikh Soedinenii, No. 5, 787–791, May, 2006. 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.
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
4.
Richa Gupta Ram Pal Chaudhary 《Phosphorus, sulfur, and silicon and the related elements》2013,188(6):735-742
Abstract 8-Methoxy-4-phenyl-3,4,5,6-tetrahydrobenzo[h]quinazoline-2(1H)-thione, obtained by the condensation of 2-benzylidene-6-methoxy-3,4-dihydronapthalene-1(2H)-one with thiourea, on reaction with chloroacetic acid and 3-chloropropanoic acid in the presence of the ionic liquid N-methylpyridinium tosylate furnishes 3-methoxy-7-phenyl-7,10-dihydro-5H- benzo[h]thiazolo[2,3-b]quinazoline-9(6H)-one and 3-methoxy-7-phenyl-5,6,10,11-tetrahydro- benzo[h][1,3]thiazino[2,3-b]quinazoline-9(7H)-one. Further, condensation of the thione with 1,2-dibromoethane and 1,3-dibromopropane yields 3-methoxy-7-phenyl-6,7,9,10-tetrahydro-5 H-benzo[h]thiazolo[2,3-b]quinazoline and 3-methoxy-7-phenyl-5,6,7,9,10,11-hexahydrobenzo [h][1,3]thiazino[2,3-b]quinazoline respectively. Arylidene derivatives have been obtained by two routes. The structures of the cyclized compounds have been established on the basis of elemental analysis and spectroscopic data. The synthesized compounds were screened for antimicrobial activity. Some of the compounds showed promising antimicrobial activities. 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.
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
7.
L. M. Potikha V. A. Kovtunenko A. V. Tarasevich J. G. Wolf Ch. André 《Chemistry of Heterocyclic Compounds》2007,43(3):347-355
We studied the dependence of the direction of conversions for salts of angular 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one
on temperature and the nature of the anion: heating in high-boiling solvents leads either to aromatization of the heterosystem
or to the rearrangement product, the linear 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one. When its hydrobromide is heated
in high-boiling solvents, along with dimerization of the linear isomers, processes of oxidation at the positions 6 and 11
of the heterosystem occur. The dimer obtained in the reaction with morpholine is readily cleaved, with formation of a 6-(4-morpholyl)-substituted
linear compound.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 430–439, March, 2007. 相似文献
8.
《Tetrahedron: Asymmetry》2001,12(2):337-340
Starting from homochiral 1,3-oxazolidine-2-thiones 1, a two-step sequence led to homotopic 2,3-dihydro-oxazolo[2,3-b]quinazolin-5-one derivatives 3. The sequence was developed and studied regarding its scope and limitations. 相似文献
9.
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
10.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2006,42(3):396-402
We have studied the reaction of 2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-one and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones
with amines, alkylating reagents, and hydrogen peroxide. We have shown that the presence of an aryl substituent at the 2 position
of [1,3-thiazino[3,2-a]benzimidazol-4-ones has a substantial effect on the direction of the reactions.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 445–452, March, 2006. 相似文献
11.
A novel 2-methylsulfanyl-4H-[1,2,4]triazolo[1,5-a]quinazolin-5-one was synthesized using dimethyl-n-cyanoimidodithiocarbonate and 2-hydrazinobenzoic acid as building blocks. Chemical transformation of the inherent lactam moiety in the targeted 2-methylsulfanyl-[1,2,4]triazolo[1,5-a]quinazolin-5-one offered access to a variety of derivatives. 相似文献
12.
Shaabani A Farhangi E Rahmati A 《Combinatorial chemistry & high throughput screening》2006,9(10):771-776
Tetraheterocyclic benzimidazo[1,2-a]quinazolin-4(1H)-one and tetrahydro-1,2,4-triazolo[5,1-b]quinazolin-8(4H)-one were synthesized in relatively high yields by the condensation reaction of an aldehyde and a cyclic beta-diketone with 2-aminobenzothiazole, 2-aminobenzimidazole or 3-amino-1,2,4-triazole without using any catalyst under solvent-free conditions. 相似文献
13.
H. K. Gakhar Anju Jain J. K. Gill Shashi Bhushan Gupta 《Monatshefte für Chemie / Chemical Monthly》1983,114(3):339-342
3-Methyl-6H-[1,2,4]triazolo[4′,3′: 4,5] [1,3,4]thiadiazolo[2,3-b]quinazolin-6-one (6) has been synthesized by the condensation of isatoic anhydride (1) with 4-amino-5-mercapto-3-methyl-[1,2,4]triazole (2) and final cyclisation of the intermediate3 with POCl3 and PCl3. Alternatively6 could also be synthesized by the condensation of 3-amino-2-mercapto-3H-quinazolin-4-one (7) withN-carbethoxy hydrazine in presence of hydrochloric acid and final cyclisation of the intermediate8 with acetic acid. The structures have been confirmed on the basis of IR, PMR and analytical results. 相似文献
14.
The synthesis of 11H-pyrido[2,1-b]quinazolin-11-one (IV) and derivatives, by the condensation of o-chlorobenzoic acid and 2-aminopyridine in DMF is reported. 相似文献
15.
The alkylation of 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one proceeds at N(6) or C(–) depending on the type of alkylating agent and reaction conditions. C(–)-Alkylation occurs in the presence of base. The secondary alkylation of the 7-alkyl derivatives occurs at the same position under these conditions. Depending on the conditions, the reaction with o-xylylene dibromide leads to spiro[5H-isoquino[2,3-a]quinazolin-7(12H).2-indane]-5-one or 11-oxo-4b,5,10,16-tetrahydro-11H-10a-azonia-15b-azadibenz[a,e]pleiadene bromide, which are derivatives of new heterocyclic systems.Communication 8, see ref. [1].See also Letter to Editor [2].Taras Shevchenko Kiev University, 252017 Kiev, Ukraine. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 643–652, May, 2000. 相似文献
16.
L. M. Potikha R. M. Gutsul V. A. Kovtunenko G. G. Dubinina A. A. Tolmachev 《Chemistry of Heterocyclic Compounds》2008,44(5):585-593
It was shown that 6-acyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-ones are formed when 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one
is heated with the chlorides and anhydrides of carboxylic acids in the presence of bases (pyridine, NaOAc) while 5-acyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-ones
are formed in the presence of NaH. In the presence of NaH 6-acyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-ones form the
products from acylation and alkylation at position 5. The action of heat on 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one
in oxalyl chloride leads to 7H,8H-2a,7a-diazacyclopenta[fg]naphthacene-1,2,8-trione.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 741–750, May, 2008. 相似文献
17.
The photochemical synthesis of 12H-benzothiazolo [2,3-b]quinazolin-12-ones (4) by the irradiation of 2-thioquinazolinediones 1 and disulphide 5 are described. 相似文献
18.
Synthesis of novel 5-methylidene-1,2,3,5-tetrahydro[2,1-b]-quinazoline derivatives 2-4 with potential biological activities mediated by alpha-adrenergic and/or imidazoline receptors was performed by reacting 2-chloro-4,5-dihydroimidazole (1) with the corresponding 2-aminoacetophenones. Compound 2, which incorporates an enamine moiety, underwent a 1,3-dipolar cycloaddition reaction with the appropriate nitrones 5-9 to give 1,2,3,5-tetrahydro-imidazo[2,1-b]quinazolin-5,5'-spiro-2',3'-diphenylisoxazol-idines 10-14. Reactions of the title compounds 2 and 4 with dimethyl acetylene-dicarboxylate (DMAD) afforded dimethyl 2-(2,3-dihydroimidazo[2,1-b]quinazolin-5(1H)-ylidenemethyl)but-2-enedioates 15, 16. Imidazo[2,1-b]quinazoline 2 was further treated with acetyl chloride, benzoyl chloride and mesyl chloride to give the 1-substituted derivatives 17, 18 and 19, respectively. The structures of all new compounds obtained were confirmed by elemental analysis and spectral data (IR, (1)H- and (13)C-NMR) as well asX-ray crystallographic analysis of 3 and 18. 相似文献
19.
I. I. Popov S. L. Boroshko B. A. Tertov S. P. Makarov A. M. Simonov B. Ya. Simkin 《Chemistry of Heterocyclic Compounds》1987,23(12):1348-1352
6(5)H-Benzimidazo[2,1-b]quinazolin-12-one was obtained in high yield by condensation of benzimidazole-2-sulfonic acid with anthranilic acid. Methods for the introduction of substituents selectively into the 5 and 6 positions of this heterocycle were developed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1673–1677, December, 1987. 相似文献
20.
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