Studies on uricosuric diuretics. II. Substituted 7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acids and 7,8-dihydrofuro[2,3-g]benzoxazole-7-carboxylic acids.

A series of substituted 7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acids 9 and 7,8-dihydrofuro[2,3-g]benzoxazole-7-carboxylic acids 12 were synthesized and evaluated for uricosuric and diuretic activities in rats. Many of the benzisoxazole derivatives 9 showed uricosuric and only weak diuretic activities, whereas the benzoxazoles 12 exhibited potent diuretic activities with little affecting urate excretion. Among these compounds, 5-chloro-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-carbo xylic acid (9b, AA-193) was found to be a potent uricosuric agent without diuretic activity and was selected for further development.     

Benzothiazolo[3,2-c]-1,3-dioxolo[4,5-g]quinazolines

Zusammenfassung Es wurde eine Reihe von 5,12a-Dihydro-6-alkyl/aryl-6H-benzothiazolo [3,2-c]-1,3-dioxolo[4,5-g]chinazoline, sowohl mitcis-als auchtrans-ständigen Wasserstoffatomen an Kohlenstoff 6 und 12a, synthetisiert. Ebenso wurden auch Verbindungen dieses Systems mit Thiazol an Position 6 hergestellt. Die Strukturen wurden mittels IR- und NMR-spektroskopischen Daten abgesichert.

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Benzothiazolo[3,2-c]-1,3-dioxolo[4,5-g]quinazolines

Some 5,12a-dihydro-6-alkyl/aryl-6H-benzothiazolo[3,2-c]-1,3-dioxolo [4,5-g]quinazolines withcis as well astrans stereochemistry of the hydrogens at carbon 6 and 12a have been synthesised. The synthesis of another series of compounds of the above system with thiazole ring at position 6 has also been accomplished. The structures have been established on the basis of IR and PMR data.

     

6-萘氧甲基-[1,3]二氧戊环并[4,5-g]喹啉-7-甲酸衍生物的合成（英文）

介绍了通过6-氯甲基-[1,3]二氧戊环并[4,5-g]喹啉-7-甲酸乙酯与1-和2-萘酚的Williamson醚合成反应及其随后的酯水解反应,"一锅法"高收率的合成了结构新颖的含有萘环结构的喹啉化合物,即2-(萘氧甲基)喹啉-3-羧酸.这种新合成的化合物可以为开发有用的药物活性先导化合物提供很好的底物.     

Synthesis and characterization of 5H-1,3-dioxolo[4,5-f]indoleethylamines

Twelve new N, N-dialkylated-5, 6-methylenedioxytryptamines and N-cyclopropyl-5, 6-methylenedioxytrypt-amine were prepared as hybrids of known psychoactive phenylethylamines and tryptamines. Novel, more convenient syntheses of N-methyl- and N-benzylcyclopropylamine are described.     

“一锅法”合成6-苯氧（苯硫）甲基-[1，3]二氧戊环并[4，5-g]喹啉-7-羧酸

以6-溴甲基-[1,3]二氧戊环并[4,5-g]喹啉-7-羧酸乙酯和酚(或硫酚)为原料,首次采用一锅法高收率地合成了6-苯氧(苯硫)甲基-[1,3]-氧戊环并[4,5-g]喹啉-7-羧酸,其结构经1H NMR,IR和元素分析表征.     

“一锅法”合成2-[(2,4-二叔丁基苯氧基)甲基]-6,7-二氧戊环并[1,3-g]喹啉-3-羧酸(英文)

采用一锅法的合成方式有效地合成了2-(2,4-二叔丁基苯氧基)甲基-6,7-二氧戊环并[1,3-g]喹啉-3-羧酸,其特点是将威廉姆逊反应和碱水解这两步反应在"一锅里"进行.所得化合物的结构经IR、1 HNMR、MS和元素分析得以证实.     

Studies on uricosuric diuretics. I. Syntheses and activities of xanthonyloxyacetic acids and dihydrofuroxanthone-2-carboxylic acids

A series of substituted xanthonyloxyacetic acids (5 and 6), 1,2-dihydrofuro[2,3-c]xanthone-2-carboxylic acids (7) and 2,3-dihydrofuro[3,2-b]xanthone-2-carboxylic acids (8) were synthesized and tested for diuretic and uricosuric activities in rats. Most of the xanthon-3-yloxyacetic acids (5) and 7 showed potent diuretic activities, while 8 had lower activities. Uricosuric activities were found in 5c, 5f, 5k, 5m, 5o, 5p, 5r, 7m, 7p and 8q.     

Synthesis of a novel heterocyclic system: 2-oxo-1,3-dioxolo[4,5-c]pyridine-6-carboxylic acid,phenylmethyl ester

The synthesis of heterobicyclic carbonate 4 and its conversions to the mixed carbonate 5 and carbamate 6 are described.     

Synthesis of some novel fused tetracyclic quinolonecarboxylic acids via 7-methyl-6,7,8,9-tetrahydro-3H-imidazo[4,5-f]quinoline and 6-methyl-5,6,7,8-tetrahydro-1H-imidazo[4,5-g]quinoline

A series of fused tetracyclic quinolonecarboxylic acids was prepared for biological evaluation. These compounds were synthesized by a route involving a regiospecific functionalization of 5-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline to obtain a series of new substituted 7-methyl-6,7,8,9-tetrahydro-3H-imidazo[4,5-f]quinolines and 6-methyl-5,6,7,8-tetrahydro-1H-imidazo[4,5-g]quinolines as convenient precursors of quinolones.     

无溶剂一锅法合成新型8-芳基-7,8-二氢-[1,3]二氧戊环并[4,5-g]喹啉-6(5H)-酮类化合物

采用微波辅助,经三组分(3,4-亚甲二氧基苯胺,2,2-二甲基-1,3-二氧六环-4,6-二酮和取代芳醛)无溶剂一锅法合成了10个新型的8-芳基-7,8-二氢-[1,3]二氧戊环并[4,5-g]喹啉-6(5H)-酮类化合物,产率75.7%~83.5%,其结构经1H NMR,FT-IR,ESI-MS和元素分析表征。     

Heterocycles containing nitrogen and sulfur. Part 49. Synthesis of derivatives of new heterocyclic systems: 1,2-Dioxocyclopenta(hexa)[g]oxazolidino-[3,2-f] pyrimido[4,5-b][1,4]thiazine, 1,2-dioxocyclopenta(hexa)-[g] imidazolidino[3,2-f]pyrimido[4,5-b][1,4]thiazine, and 1,2-oxazino[5,4-g]pyrimidino[4,5-b][1,4]thiazine

The reaction of 4-methoxy-5-amino-6-mercaptopyrimidine with 2-oxo-1-chlorocyclopentyl(hexyl)glyoxalate esters gave derivatives of the previously unknown tetracyclic systems 1,2-dioxocyclopenta (hexa)[g]oxazolidino[3,2-f]pyrimido[4,5-b][1,4]thiazines, which are transformed by ammonium acetate into derivatives of 1,2-dioxocyclopenta(hexa) [g]imidazolidino[3,2-f]pyrimido[4,5-b]-[1,4] thiazines. Derivatives of the new tricyclic 1-oxazino [5,4-g]pyrimido[4,5-b][1,4]thiazine system were obrtained by reaction of 6-carbethoxy-7-acetylpyrimido [4,5-b] [1,4] thiazines with hydroxylamine.     

New heterocyclic systems. Benzo[4,5]cyclohepta[1,2-b]pyrrole and benzo[5,6]cyclohepta[1,2-f]pyrrolizidine derivatives

The synthesis of the polycyclic pyrrole acetic acids 9e, 13e and 13g by multistep processes from 1-bromo-4-phenylbutan-2-one ( 6c ) is reported. An instance of the use of the 2-chloroethyl moiety as a pyrrole nitrogen protecting group is described. The α-methylaminoketone ( 6e ) was synthesised by a novel two step process from 6c and methyl N-methylformimidate ( 12 ).     

Imidazo [4,5-c] - and [4,5-6] pyridines

The synthesis of novel imidazo[4,5-c]pyridines 11-13 and imidazo[4,5-b]pyridines 18-20 is described using 2 as the starting material. The synthesis is generally applicable for the introduction of a wide variety of substituents.     

硅胶键合N-丙基氨基磺酸催化合成8-芳基-7,8-二氢-[1,3]二氧杂环戊烯并[4,5-g]苯并吡喃-6-酮类化合物

120℃、无溶剂条件下,硅胶键合N-丙基氨基磺酸可有效催化芝麻酚、芳香醛和米氏酸三组分一锅法合成8-芳基-7,8-二氢-[1,3]二氧杂环戊烯并[4,5-g]苯并吡喃-6-酮类化合物.考察了温度及催化剂用量对产率的影响.产物的结构经1H NMR,13C NMR,质谱和元素分析进行了表征.     

Synthesis and Reactivity of 2-(Thiophen-2-yl)[1,3]thiazolo[4,5-f]quinoline

Russian Journal of Organic Chemistry - The condensation of quinolin-5-amine with thiophene-2-carbonyl chloride in propan-2-ol gave N-(quinolin-5-yl)thiophene-2-carboxamide. Treatment of the latter...     

4'',4″(5″)-{二-[1,3]二氧[4,5-g]喹啉}-二苯并-18-冠-6的合成

6-氨基胡椒醛与4',4″(5″)-二乙酰基二苯并-18-冠-6进行Friedlnder缩合得到新的冠醚衍生物--4',4″(5″)-{二-[1,3]二氧[4,5-g]喹啉}-二苯并-18-冠-6(3),产率62%.3的结构经UV, 1H NMR, 13C NMR, IR和MS表征.     

Modified Coumarins. 10. Synthesis of Substituted 2-(7-Oxofuro[3,2-g]chromen-6-yl)acetic Acids

Substituted 2-(7-oxofuro[3,2-g]chromen-6-yl) acetic acids, modified psoralen analogs, were synthesized by linear fusion of a furan ring to the coumarin system.     

1,4-Cycloaddition reactions. II. Preparation of p-dioxino[2,3-g]furo[3,2-c] quinolines,p-dioxino[2,3-f] furo[3,2-c] quinolines,and [1,3] dioxolo[4,5-g] furo[3,2-c] quinolines from 2,3-dihydro-5-methylfuran and schiff bases

The boron trifluoride catalyzed 1,4-addition of 2,3-dihydro-5-methylfuran to N-(p-methoxy-benzylidene)-1,4-benzodioxan-6-amine (II) gave 2 pairs of epimers, 2,3,3a,4,5,8,9,11b-octahydro-4-(p-methoxyphenyl)-11b-methyl-p-dioxino[2,3-g]furo[3,2-c]quinoline (IIIa and b) and 2,3,7,8,8a,9.10,1la-octahydro-8-(p-methoxyphenyl)-11a-methyl-p-dioxino[2,3-f]furo[3,2-c]quinoline (IVa and b). When N-(p-methoxybenzylidene)-3,4-methylenedioxyaniline (V) was condensed with 2,3-dihydro-5-methylfuran in an analogous manner, a mixture of 2 epimers of 2,3,3a,4,5,10b-hexahydro-4-(p-methoxyphenyl)-10b-methyl[1,3]dioxolo[4,5-g]furo[3,2-c]quinoline (VIa and b) was isolated. Treatment of this mixture with sulfur afforded 6-(p-methoxyphenyl)-8-methyl-1,3-dioxolo[4,5-g]quinoline-7-ethanol (VIII). Structural assignments for all of the products were made from NMR spectra. None of the compounds possessed appreciable biological activity.