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1.
2,4-Dimethyl-7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid on preparation of a mixed anhydride, followed by reduction with sodium borohydride, affords 5,7a,13,13b-tetramethyl-2,10-dinitro-5a,7,7a,13,13a,13b-hexahydro-5H-[1,4]benzoxazino[3′,2′:4,5]pyrano[3,2-b][1,4]benzoxazine (3), the structure of which was established unambiguously by X-ray analysis. 相似文献
2.
Marianne R. Spada Robert S. Klein Brian A. Otter 《Journal of heterocyclic chemistry》1989,26(6):1851-1857
The utility of certain 5-alkynyloxy-, 5-alkynylthio, and 5-alkynylsulfinyl-pyrimidines as precursors of 7-substituted furo[3,2-d]- and thieno[3,2-d]pyrimidines has been examined. When treated with sodium methoxide in warm methyl sulfoxide, 1,3-dimethyl-5-(2-propynyloxy)uracil ( 6 ) cyclizes to afford 1,3,7-tri-methylfuro[3,2-d]pyrimidine-2,4-(1H,3H)-dione ( 12 ) in 52% yield, possibly via the allenic ether 9 (R = H). The corresponding 5-(2-butynyloxy)pyrimidine ( 7 ), obtained in good yield by treating 6 with methyl iodide and sodium hydride in methyl sulfoxide, fails to undergo an analogous cyclization. However, compound 7 does undergo a normal alkynyl Claisen rearrangement and cyclization when heated at 130°, giving the 8-methylpyrano[3,2-d]pyrimidine 8 in methyl sulfoxide and the 6,7-dimethylfuro[3,2-d]pyrimidme 11 in dimethylformamide. The 5-(2-propynylthio)pyrimidine 15 affords the allene 19 and the 1-propyne 22 when treated with various bases, but none of the 7-methylthieno[3,2-d]pyrimidine 16. At 145° in methyl sulfoxide, 15 undergoes a thio-Claisen rearrangement process to afford the 6-methylthieno[3,2-d]pyrimidine 17 together with substantial amounts of a product 20 that bears a 7-thiomethoxymethyl substituent derived from the solvent. Heating the 5-(2-propynylsulfinyl)pyriniidine 23 at 105° in methyl sulfoxide, followed by acidification of the reaction mixture, affords 1,3-dimethyl-7-formylthieno[3,2-d]pyrimidine-2,4-(1H,3H)-dione ( 29 ) in 47% yield. Deuterium labelling studies established that the aldehyde proton of 29 is derived from the 3′-proton of 23 . This finding is consistent with a mechanism that involves sequential [2,3] and [3,3] sigma-tropic rearrangements, and the intermediacy of a dihydrothieno[3,2-d]pyrimidine such as compound 30. 相似文献
3.
Bongui JB Elomri A Cahard D Tillequin F Pfeiffer B Pierré A Seguin E 《Chemical & pharmaceutical bulletin》2005,53(12):1540-1546
Condensation of 1-bromo-2-naphthalenecarboxylic acid (9) with 7-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamine (13) followed by acid-mediated cyclization afforded 6-methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2-h]acridin-7-one (15), which was further methylated into 6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2-h]acridin-7-one (benzo[c]acronycine) (3) and 6,7-dimethoxy-3,3-dimethyl-3H-benzo[c]pyrano[3,2-h]acridine (4). Osmium tetroxide oxidation of 15 gave the (+/-)-cis-diol 16, which afforded the benzopyranoacridine and benzopyranoacridone esters 17-22 upon acylation. Condensation of 9 with suitable aminoquinolines 23-25 afforded the carboxylic naphthylquinolylamines 26-28. Cyclization gave the corresponding naphtho[1,2-b][1,10]-phenanthrolin-7(14H)-ones 29 and 30, and naphtho[1,2-b][1,7]-phenanthrolin-7(14H)-one 31, which were subsequently N-methylated to the desired 14-methylnaphtho[1,2-b][1,10] and [1,7]-phenanthrolinones 6, 7, and 8. Benzo[c]pyrano[3,2-h]acridin-7-one derivatives 3, 16, and 22 displayed cytotoxic activities within the same range of magnitude as acronycine itself, whereas 7-alkoxybenzo[c]pyrano[3,2-h]acridine and 7-acyloxybenzo[c]pyrano[3,2-h]acridine derivatives 4 and 17-21 were less active when tested against L1210 murine leukemia cells in vitro. Naphthophenanthrolinones 6-8 were devoid of significant antiproliferative activity, but compounds 29-31 bearing no substituent on the nitrogen atom at position 14 were more potent. 相似文献
4.
L. M. Potikha V. A. Kovtunenko A. V. Tarasevich 《Chemistry of Heterocyclic Compounds》2007,43(12):1551-1558
Oxidation of the hydrobromide of 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one with dimethyl sulfoxide leads to 11-hydroxy-11H-isoquino[3,2-b]quinazoline-6,13-dione,
and with hydrogen peroxide to the hydrobromide of 2-[(4-oxo-3,4-dihydro-2-quinazolinyl)carbonyl]benzoic acid. Salts of 5-and
6-alkyl-substituted isoquino[3,2-b]quinazolines are readily oxidized on boiling in nitrobenzene, which leads to aromatization
of the isoquino[3,2-b]quinazoline system to 5-methyl-13-oxo-5H,13H-isoquino[ 3,2-b]quinazolinium perchlorate and 6-benzyl-13H-isoquino[3,2-b]quinazolin-13-one.
The structures of the dehydrogenation products were established from 1H NMR and UV spectra. The interaction of the obtained compounds with NaBH4 has been studied.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1833–1840, December, 2007. 相似文献
5.
Channabasappa Sannappa Angadiyavar Srinivasa Rajagopal 《Monatshefte für Chemie / Chemical Monthly》1968,99(3):1014-1019
Zusammenfassung Eine für die Synthese linearer Furoxanthone ohne Substituenten am Furanring geeignete Methode ist dieUllmann-Kondensation von 6-Hydroxycumaran mit verschiedenen o-Chlorbenzoesäuren mit anschließender Cyclisierung und Dehydrierung. Als Beispiele werden die Synthesen von Furo[3,2-b]-, 7-Methylfuro-[3,2-b]-und 8-Methylfuro[3,2-b]xanthon beschrieben.
Diese Veröffentlichung ist ein Teil der Dissertation, dieC. S. Angadiyavar an der Karnatak University zur Erlangung des Titels eines Ph. Dr. einreichen wird.
10. Mitt.:Y. S. Agasimundin undS. Rajagopal, Chem. Ber.100, 383 (1967). 相似文献
A method for the synthesis of linear furoxanthones carrying no substituent in the furan ring is achieved by theUllmann condensation of 6-hydroxycoumaran with various o-chlorobenzoic acids, followed by cyclisation and subsequent dehydrogenation. This is illustrated by the synthesis of furo[3,2-b]-, 7-methylfuro[3,2-b]-and 8-methylfuro[3,2-b]xanthones.
Diese Veröffentlichung ist ein Teil der Dissertation, dieC. S. Angadiyavar an der Karnatak University zur Erlangung des Titels eines Ph. Dr. einreichen wird.
10. Mitt.:Y. S. Agasimundin undS. Rajagopal, Chem. Ber.100, 383 (1967). 相似文献
6.
Katherine Buggle Úna Ní Ghógáin Patrick MacManus 《Monatshefte für Chemie / Chemical Monthly》1988,119(8-9):945-951
The conversion of 2H-[1]benzothieno[3,2-b]pyran-2-ones into mono- and dithio-derivatives and the preparation of some dibenzothiophenes, sulphines and pyridones are described.
Einige Reaktionen von 2H-[1]Benzothieno[3,2-b]pyran-2-onen und verwandten Verbindungen
Zusammenfassung Es wird die Umsetzung von 2H-[1]benzothieno[3,2-b]pyran-2-onen zu Monound Dithio-Derivaten und die Darstellung einiger Dibenzothiophene, Sulfine, und Pyridone beschrieben.相似文献
7.
The reaction of 6-aminoeoumarin with some ethoxymethylene compounds and dimethyl acetylenedicarboxylate led to condensation products which on thermal cyclizations afford new derivatives of 3H-pyrano[3,2-f]quinoline (IIa-IIc). 相似文献
8.
Summary 6-Phenyl-1,3-dimethyl-2,4-dioxo-1,2,3,4,8,9-hexahydro-[1,3,5]-thiadiazepino-[3,2-f]-purine (5) was obtained by a three-step synthesis from 8-mercapto-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione (1) and 2-(benzoylamino)-ethyl chloride (2)via 8-(benzoylaminoethylthio)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione (3) and its chloromido derivative4. The analogous 9-phenyl-1,3-dimethyl-2,4-dioxo-1,2,3,4,6,7-hexahydro-[1,3,6]-thiadiazepino-[3,2-f]-purine (7) was synthesized either from compound1 and N-(2-chloroethyl)-benzimido chloridevia N-(chloroethyl)-S-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-7H-purin-8-yl)-benzothioimide (6), or alternatively from 7-(2-benzoylaminoethyl)-8-bromo-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione (9), its 8-mercapto derivative10 and the corresponding chloroimido compound11 being the intermediates.Part of this paper was presented as a preliminary report at the Congress of Czech and Slovak Chemical Societies, Olomouc, Czech Republic, September 13–16, 1993 相似文献
9.
Keitaro Senga Kiyoko Fukami Hashime Kanazawa Sadao Nishigaki 《Journal of heterocyclic chemistry》1982,19(4):805-808
New synthetic routes to pyrido[3,2-d]pyrimidines starting with 5-amino-1,3,6-trimethyluracil (I) or 1,3,6-trimethyl-5-nitrouracil (X) are described. Thus, condensation of I with arylaldehydes gave 5-arylideneamino-1,3,6-trimethyluracils (IIa-h), which upon heating with dimethylformamide dimethylacetal afforded 6-aryl-1,3-dimethylpyrido[3,2-d]pyrimidine-2,4(1H,3H)-diones (Va-h) via 5-arylideneamino-1,3-dimethyl-6-(2-dimethylaminovinyl)uracils (IIIa-h). On the other hand, reaction of X with phenylacetaldehyde in the presence of base yielded Va and its 5-oxide (XI). 相似文献
10.
Sunil Sinha Anil Tyagi R. K. Pandey B. C. Joshi 《Journal of heterocyclic chemistry》1985,22(1):235-237
Synthesis and medicinal importance of 4-methyl-6-nitro-8,9,10,11-tetrahydro-2H-benzofuro[2,3-b]-1-benzo-pyran-2-one (I), 4-ethyl-11-nitro-6,7,8,9-tetrahydro-2H-benzofuro[3,2-g]-1-benzopyran-2-one (II), and 6,7-di-hydro-4,13-dimethylbis-1-benzopyrano[6,7-d:7′,6′-d']-2H,11H-benzo[1,2-b:3,4-b']difuran-2,11-dione (III) is presented. The structures of these compounds were confirmed by elemental analysis and spectral studies. 相似文献
11.
A convenient and rapid synthesis of hitherto unknown 3-aroyl-4-aryl-2-phenylamino-4H-benzo[g]chromene-5,10-diones in high yield from β-aroyl-thioacetanilide, aromatic aldehyde, and 2-hydroxy-1,4-naphthoquinone via InCl3 catalyzed one-pot three-component tandem Knoevenagel condensation–Michael addition–intramolecular cyclization–elimination reaction sequence is disclosed for the first time. This domino protocol has been used to obtain highly substituted pyrano[3,2-c]chromen-5(4H)-ones and 7,7-dimethyl-7,8-dihydro-4H-chromen-5(6H)-ones from N,3-diaryl-3-oxo-propanethioamide, aromatic aldehyde, and 4-hydroxycoumarine or dimedone under mild reaction conditions. A plausible reaction mechanism is proposed. The 4H-pyrano[3,2-c]chromen-5-one and 7,7-dimethyl-7,8-dihydro-4H-chromen-5(6H)-one derivatives possessing 3-(2-chlorobenzoyl)-2-phenylamino-substituents further cyclized under basic conditions to yield penta-cyclic 7,13-diaryl-5,14-dioxa-13-aza-benzo[a]naphthacen-6,8(7H,13H)-dione and tetra-cyclic 6,12-diaryl-3,3-dimethyl-3,4-dihydro-2H-chromeno[2,3-b]quinolin-1,11(6H,12H)-dione, respectively. 相似文献
12.
A series of 3-substituted [1]benzothieno[3,2-d]pyrimidine derivatives has been synthesized as possible antileukemic agents by condensation of methyl 3-(ethoxymethylene)amino-2-benzothiophene carboxylate (II) with a variety of amines to afford the corresponding 3-aryl and 3-alkyl [I]benzothieno[3,2-d]pyrimidin-4(3H)-ones, Ill and IV, respectively. In addition, Mannich reactions of [I]benzothieno[3,2-d]pyrimidin-4(3H)-one (VIII) with formaldehyde and secondary amines gave the expected derivatives, IX. 3-Amino[I]benzothieno[3,2-d]-pyrimidin-4(3H)-one (VI) reacted with substituted aromatic aldehydes in the presence of boron trifluoride to yield the corresponding imines VII. 相似文献
13.
A method for the synthesis of previously unknown pyrido[3´,2´:4,5]thieno[3,2-c]isoquinolin-5(6H)-ones was suggested, which includes a condensation reaction of substituted 3-cyanopyridine-2(1H)-thiones with methyl 2-(chloromethyl)benzoate and subsequent treatment of the condensation products with potassium tert-butoxide. The oxidation of the condensation products to sulfoxides or sulfones and subsequent treatment of these compounds with potassium tert-butoxide led to substituted pyrido[3´,2´:4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11-oxides or substituted pyrido[3´,2´:4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11,11-dioxides.
相似文献14.
Kuppuswamy Nagarajan Patrick J. Rodrigues Munirathinam Nethaji Markus Vhler Wolfgang von Philipsborn 《Helvetica chimica acta》1994,77(1):155-163
Condensation of 3,4-dihydro-6,7-dimethoxyisoquinoline ( 4 ) with 4-methylnicotinoyl chloride ( 12 ) in refluxing pyridine gives 5,6,13,13a-tetrahydro-2,3-dimethoxy-8H-isoquino[2,1-b][2,7] naphthyridin-8-one ( 11 ), along with some of its 13,13a-didehydro derivative 7 . A similar reaction of 4 with 4-(chloromethyl)nicotinoyl chloride ( 14 ) affords, in addition to 7 , the isomeric product 10,11-dihydro-7,8-dimethoxy-13H-pyrido[4′,3′:3,4]pyrrolo[2,1- b][3]benzazepin-13-one ( 3 ). Analogous pairs of products are obtained from 3,4-dihydro-6,7-(methylenedioxy)- and 3,4-dihydro-6,7,8-trimethoxy-isoquinolines ( 15 and 18 , resp.). The structure of 3 was established by extensive NMR data and confirmed by single-crystal X-ray studies. Structure 7 has the ring system of the Alangium alkaloids like alangimarinc ( 1 ), while the isomeric ring system 3 is predicted to be present in nature on biogenetic reasoning. 相似文献
15.
Methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 3-amino-5,5-dimethylcyclohex-2-en-1-one having no substituent on the nitrogen atom to give 3-aroyl-4-arylamino-6′,6′-dimethyl-6′,7′-dihydro-5H-spiro[furan-2,3′-indole]-2′,4′,5′(1′H,5′H)-triones or methyl 12-aroyl-11-aryl-9-hydroxy-5,5-dimethyl-3,10-dioxo-8,11-diazatricyclo[7.2.1.02,7]dodec-2(7)-ene-1-carboxylates. The latter underwent thermal recyclization to 3′-aroyl-1′-aryl-4′-hydroxy-6,6-dimethyl-6,7-dihydrospiro[indole-3,2′-pyrrole]-2,4,5′(1H,1′H,5H)-triones. 相似文献
16.
V. V. Lipson S. M. Desenko V. V. Borodina M. G. Shirobokova V. I. Musatov 《Russian Journal of Organic Chemistry》2005,41(1):114-119
Three-component condensation of 3,5-diamino-1,2,4-triazole with aromatic aldehydes and dimedone in dimethylformamide gives 2-amino-5-aryl-8,8-dimethyl-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[3,2-b]quinazolin-6-ones. The reaction of 3,5-diamino-1,2,4-triazole with dimedone in the absence of aldehyde involves dimethylformamide as one of the carbonyl components to afford 2-amino-8,8-dimethyl-6,7,8,9-tetrahydro[1,2,4]triazolo[2,3-a]quinazolin-6-one.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 115–120.Original Russian Text Copyright © 2005 by Lipson, Desenko, Borodina, Shirobokova, Musatov. 相似文献
17.
Tadasu Tanaka Takeo Iwakuma Mitsuyoshi Wagatsuma Ikuo Iijima 《Journal of heterocyclic chemistry》1972,9(6):1355-1358
This paper describes the syntheses and the properties of 1H-pyrrolo[2,3-6]quinolines derived from 2,3-dihydrofuro[3,2-c]quinolines or 3-(β-chloroethyl)-2,4-dichloroquinolines. The discrepancy on the physical data of 1H-pyrrolo[2,3-b]quinoline between our product and Perkin's previously reported product is also discussed. 相似文献
18.
V. V. Dabaeva M. R. Bagdasaryan A. S. Noravyan 《Chemistry of Heterocyclic Compounds》2011,47(5):639-643
The reactions of 2-methyl (propyl) substituted 8,8-dimethyl-7,10-dihydro-4H,8H-pyrano[3",4":5',6']pyrido[3',2':4,5]thieno[3,2-d][1,3]oxazines
with primary amines give 2-methyl (propyl) substituted 8,8-di- methyl-7,10-dihydro-8H-pyrano[3",4":5',6']pyrido[3',2':4,5]thieno[3,2-d][1,3]pyrimidin-4(3H)-ones
or 3-acetyl-N-alkyl- and N-alkyl-3-butyrylamino-7,7-dimethyl-7,8-dihydro-5H-pyrano[4,3-b]thieno[3,2-e]- pyridine-2-carboxamides depending on steric hindrance in the amines. 相似文献
19.
Laurent A. Dcostered Kurt Hostettmann Helen Stoeckli-Evans Jerome D. Msonthi 《Helvetica chimica acta》1987,70(7):1694-1702
Two new 2H-1-benzopyranyl ketones 1 and 2 and three new pyrano[3,2-c: 4,5,6-d′ e′]di[1]benzopyrandiyl diketones 3 , 4a / 4b , and 5 have been isolated from the leaves and twigs of Hypericum revolutum VAHL (Guttiferae). The structure of 3 (hyperevoline) was established by X-ray analysis as 1,1′-[1,13,13a,13b-tetrahydro-5,8,10-trihydroxy-2,2,6,9,13,13-hexamethyl-2H, 7aH-pyrano[3,2-c:4,5,6-d′e′]di[1]benzopyran-4, 11-diyl]bis[2-methyl-1-propanone]. The structures of the isolated compounds were established by spectroscopic (UV, IR, EI-MS, 1H- and 13C-NMR) and chemical (acetylation and acidic dimerization) methods. 相似文献
20.
Yu. P. Andreichikov G. E. Trukhan S. N. Lyubchenko G. N. Dorofeenko 《Chemistry of Heterocyclic Compounds》1976,12(2):205-210
Isochromylium cations containing easily detached groupings (NHCOR, NH2, OCH3) in the 3 position react readily with o-phenylenediamine. The reaction is accompanied by opening of the benzopyrylium ring and condensation of the resulting compound at one or two amino groups of o-phenylenediamine. Benzimidazo[3,2-b]isoquinolinium salts were synthesized alternatively by acylation of 2-(3,4-dimethoxybenzyl)benzimidazole. The tautomerism of the synthesized N-(2-aminoaryl)isoquinolinium perchlorates was investigated.See [1] for communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 238–243, February, 1976. 相似文献