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1.
Robert Y. Ning George F. Field Leo H. Sternbach 《Journal of heterocyclic chemistry》1970,7(3):475-478
The cyclic nitrones 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide ( 5a ) and 1,3-dihydro-7-methylthio-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide ( 5b ) are photoisomerized to readily isolable oxaziridines, 7-chloro-4,5-epoxy-5-phenyl-1,3,4–5-tetrahydro-2H-1,4-benzodiazepin-2-one ( 6a ) and 4,5-epoxy-5-phenyl-1,3,4,5-tetrahydro-7-methylthio-2H-1,4-benzo-diazepin-2-one ( 6b ). Oxaziridine 6b upon further irradiation gave ring expansion and ring contraction products, 4,6-dihydro-2-phenyl-9-methylthio-5H-1,3,6-benzoxadiazocin-5-one ( 7b ) and 4-benzoyl-3,4-dihydro-6-methylthioquinoxalin-2(1H)-one ( 8b ) respectively. The ring contraction product, 4-benzoyl-6-chloro-3,4-dihydroquinoxalin-2(1H)-one ( 8a ), was obtained from irradiation of oxaziridine 6a . 相似文献
2.
Photolysis of N-benzyl-N-phenylearbamoylazide (IVc) afforded 1-benzy 1-2-benzimidazolinone (Ic), 2-benzimidazolinone (IIe), 4-benzy 1-2-benzimidazolinone (IIe), and 5-benzy1-2-benzimidazo-linone (IIf)- The same reaction of N-benzyl-N-(4-chlorophenyl) carbamoyl azide (IVd) gave 3-benzyl-1-(phenylhydrazocarbonyl)-2-benzimidazolinone (VIb) besides the above four products. In the case of N-benzyl-4-(4-butoxyphenyl)carbamoyl azide (IVe), 1-benzy1-5-butoxy-2-benz-imidazolinone (1e), 5-butoxy-2-benzimidazolinone (IId), 5-benzy1-2-benzimidazolinone (IIf), and 4-benzy1-6-butoxy-2-benzimidazolinone (IIg). 相似文献
3.
Two new phenylpentadienamides isolated from the culture filtrate of Streptomyces sp. were assigned the structures 5-(4-aminophenyl)penta-2,4-dienamide ( 2 ) and N2-[5-(4-aminophenyl)penta-2,4-dienoyl]-L -glutamine ( 3 ). In addition, 5-(4-aminophenyl)penta-2,4-dienoic acid ( 1 ) has been isolated, and its spectroscopic characteristics are reported for the first time. Compounds 1–3 exist in both the (2E,4E)- and (2E,4Z)-configurations. Electrospray and tandem MS, and HPLC/MS proved to be particularly suitable for the characterization of these metabolites. 相似文献
4.
Gerhard W. Fischer 《Journal of heterocyclic chemistry》1994,31(6):1529-1534
The acid-catalyzed reaction of 1-aryl-5-(2-dimethylaminovinyl)-1H-tetrazoles 2 with arylamines suitably functionalized in the ortho-position resulted in Z-configurated transamination products which were cyclized to novel 3-tetrazolylquinolines by the action of sodium ethoxide. Thus, on reacting 2 with 2-aminoacetophenone or 2-aminobenzophenone, respectively, the 2-[2-(1-aryl-1H-tetrazol-5-yl)vinyl-amino]aryl ketones 3a-g were obtained, the cyclization of which gave 4-substituted 3-(1-aryl-1H-tetrazol-5-yl)quinolines 4 . In the case of the transamination products 3h-1 , prepared from 2 and methyl anthranilate, the ring closure afforded 3-(1-aryl-1H-tetrazol-5-yl)-1H-quinolin-4-ones 5 . Starting from 2 and anthranilonitrile 4-amino-3-(1-aryl-1H-tetrazol-5-yl)quinolines 10 were obtained via the corresponding intermediates 9 . 相似文献
5.
Yihua Zhang Anna-Britta Hmfeldt Salo Gronowitz 《Journal of heterocyclic chemistry》1995,32(3):771-777
5-(2-, 3- and 4-Pyridyl)-2-t-butoxythiophenes have been prepared in very good yields by Pd(0) catalyzed cross-coupling of the three isomeric bromopyridines with 5-trimethylstannyl-2-t-butoxythiophene derived from 2-bromothiophene via 2-t-butoxythiophene. Dealkylation of 5-(2-, 3- and 4-pyridyl)-2-t-but-oxythiophenes with boron trifluoride etherate in dichloromethane at room temperature led to predominant formation of rearranged products, 5-(2- and 3-pyridyl)-3-t-butyl-3-thiolene-2-ones, together with a small amount of 5-(2- and 3-pyridyl)-2-hydroxythiophenes as a mixture of two tautomeric keto forms in the case of the 2-pyridyl and the 3-pyridyl isomers, and exclusive formation of rearranged product in the case of the 4-pyridyl isomer. However, dealkylation of 2-methoxy-5-(2-, 3- and 4-pyridyl)thiophenes, prepared similarly to the 5-(2-, 3- and 4-pyridyl)-2-t-butoxythiophenes, with boron tribromide under the same reaction conditions as above resulted exclusively in the tautomeric mixture of 5-(2- and 3-pyridyl)-3-thiolene-2-ones and 5-(2- and 3-pyridyl)-4-thiolene-2-ones in the case of the 2-pyridyl and 3-pyridyl isomers. In the case of the 4-pyridyl isomer polymerization took place. 相似文献
6.
J. W. Mcfarland J. J. Beaulieu L. N. Arrey L. M. Frey 《Journal of heterocyclic chemistry》1988,25(5):1431-1434
4-Toluenesulfonyl isocyanate cyclized with 1,2-epoxy-3-phenoxypropane and 2,3-epoxypropyl 4-methoxyphenyl ether, respectively, to give 3-(4-toluenesulfonyl)-5-phenoxymethylene-2-oxazolidone ( I ) and 3-(4-toluenesulfonyl)-5-(4-methoxyphenoxymethylene)-2-oxazolidone ( II ). Compounds I and II were hydrolyzed in 2 M sodium hydroxide solution to the corresponding uncyclized hydroxy amides, VII and VIII. Compound I was remarkably stable toward 6 M hydrochloric acid and amines. Styrene oxide, 1,2-epoxybutane, 3-chloro-1,2-epoxypropane, and 1-methoxy-2-methylpropylene oxide reacted with the isocyanate to afford 3-(4-toluene-sulfonyl)-4-phenyl-2-oxazolidone (III), 3-(4-toluenesulfonyl)-4-ethyl-2-oxazolidone ( IV ), 3-(4-toluenesulfonyl)-5-chloromethyl-2-oxazolidone ( V ), and 3-(4-toluenesulfonyl)-4,4-dimethyl-5-methoxy-2-oxazolidone ( VI ), respectively. The yield of VI was constant over a temperature range of 25–90°. 相似文献
7.
Reaction of readily available 2-methyl-4-formylthiazole ( 1 ) with glyoxal and ammonia gave 2-(2-methyl-4-thiazolyl)imidazole ( 2 ). Nitration of 2 with a mixture of nitric acid-sulfuric acid at 100° yielded 2-(2-methyl-4-thiazolyl)-4,5-dinitroimidazole ( 3 ) as the sole reaction product, while nitration at 65° afforded 2-(2-methyl-4-thiazolyl)-4-(or 5)-nitroimidazole ( 4 ). N-Methylation of compound 4 in the presence of base gave 1-methyl-2-(2-methyl-4-thiazolyl)4-nitroimidazole ( 6 ), whereas N-methylation with diazomethane afforded 1-methyl-2-(2-methyl-4-thiazolyl)-5-nitroimidazole ( 5 ). N-Methylation of compound 3 yielded 1-methyl-2-(2-methyl-4-thiazolyl)-3,5-dinitroimidazole ( 7 ) in high yield. 相似文献
8.
5-Hydroxy-7-alkyl-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitriles (VIIb-d) and 5-hydroxy-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid, ethyl ester (VIIa) were prepared from 5-carbethoxy-4-chloro-2-phenylpyrimidine (IV) via 4-[(cyanomethyl)alkylamino[-2-phenyl-5-pyrimidinecarboxylic acid, ethyl esters (Vb-d) and 4-[(carboxymethyl)amino]-2-phenyl-5-pyrimidinecarboxylic acid, diethyl ester (Va), respectively. The hydroxy group of the pyrrolo-[2,3-d]pyrimidines could be methylated, acetylated and tosylated. Hydrolysis of 5-methoxy-7-methyl-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile (IX) afforded the corresponding amide (X). 相似文献
9.
The synthesis of 2,2-bis(hydroxymethyl)-4-methyl-5-phenylfuran-3(2H)-one ( 9 ), 5-[(1S,2S,Z)-1,2-(ethylidenedioxy)hex-3-enyl]-2,2-bis(hydroxymethyl)-4-methylfuran-3(2H)-one ( 24 ), and 5-[(1S,2S,Z)-1,2-(ethylidenedioxy)hex-3-enyl]-2-(hydroxymethyl)-4-methylfuran-3(2H)-one ( 28 ), which represent more advanced, suitably functionalized intermediates for the synthesis of pseurotin A ( 1 ), a secondary metabolite of Pseudeurotium ovalis STOLK , is described. 相似文献
10.
Gerhard W. Fischer 《Journal of heterocyclic chemistry》1993,30(6):1517-1519
Tetrazolyl-substituted enamino ketones 1 react with various amidines 2 to give 5-(1-phenyl-1H-tetrazol-5-yl)pyrimidines 3 . In the case of the chloroacetyl enamine 4 4-(N,N-dimethylaminomethyl)-substituted tetra-zolylpyrimidines 5 were obtained. Subsequent hydrolysis of the 4-trifluoromethyl derivatives 3b, 3d and 3g afforded the corresponding 5-(1-phenyl-1H-tetrazol-5-yl)pyrimidine-4-carboxylic acids 6 . 相似文献
11.
2,4-Diamino-6-(p-aminophenethyl)pyrimidines with a 5-phenylbutyl (XIX) and 5-(p-chlorophenyl) (VIII) substituent were synthesized by condensation of the corresponding pyrimidine-6-carboxaldehydes (XVI, X) with the Wittig reagent derived from p-nitro-benzyl bromide, followed by catalytic hydrogenation. Selective bromoacetylation of VIII and XIX afforded the candidate active-site-directed irreversible inhibitors of dihydrofolic reductase, namely, 6-(p-bromoacetamidophenethyl)-2,4-diaminopyrimidine with a 5-(p-chlorophenyl)- (IV) and 5-phenylbutyl- (III) substituents. Although III and IV were excellent reversible inhibitors of dihydrofolic reductase, neither showed any inactivation of the enzyme; in contrast, the corresponding 2-amino-6-(p-bromoacetamidophenethyl)-5-phenylbutyl-4-pyrimidinol (II) - which differs from III only in the 4-substituent (NH2 vs. OH) - was an excellent active-site-directed irreversible inhibitor of dihydrofolic reductase, but II was a poor reversible inhibitor. Thus the conformations of II and III are most probably different when complexed to dihydrofolic reductase. 相似文献
12.
The iminium salt, N,N-dimethyl-N-[2-(2-phenyl-4H-l-benzopyran-4-ylidene)ethylidene] imin-ium perchlorate ( 3 ), reacts with secondary amines by exchanging the dimethylimino group for the added amine. Primary amines also reacted with 3 in the same manner. The bis iminium salts, N,N,N',N'-tetramethyl-N,N'-[2-(2-phenyl-4H-l-benzopyran-4-ylidene)-1,3-propanediylidene]-bis(immium perclilorate) ( 4 ) and the corresponding thiapyran derivative ( 5 ), react with ammonia to give 5-dimethylamino-2-phenyl-5H-1-benzopyrano[3,4-c]pyridine ( 10 ) and the thia analog 11 . The reactions of 4 and 5 with primary amines give 3-alkyl-5-dimethylamino-2-phenyl-5H-l-beiizopyrano[3,4-c]pyridinium perclilorate salts or the corresponding thiapyrano compounds. Compounds 4 and 5 react with secondary amines by exchanging the dimethylimino groups with the secondary amine and addition of the amine at the 2-position of the pyran or thiapyran ring. 相似文献
13.
Hans Zimmer M. J. Manning M. Ventura Adel Amer Abdel Monem El Massry 《Journal of heterocyclic chemistry》1986,23(1):199-201
The reduction of 4-aroyl-3-hydroxy-2(5H)-furanons 1a-c was investigated using different reducing agents. Sodium borohydride reacts with type 1 compounds by loss of water to yield 4-(arylmethylene)-2,3(4H,5H)-furandiones 2a-c . Platinum or charcoal supported by pallodium chloride transforms 1a to 4-benzyl-3-hydroxy-2(5H)-furanone ( 3). Compounds 2a and 2b react with o-phenylenediamine to give 3-(E-(1′-hydroxymethyl-2′-aryl)ethenyl]-2-quinoxalinones 4a and 4b . The lactone 3 under the same conditions splits out formaldehyde and forms 3-(2′-phenylethyl)-2-quinoxalinone ( 6 ). The structure assignments of the novel compounds are based on elemental analysis and nmr as well as ir spectroscopic data. 相似文献
14.
Katsumi Tabei Etsuko Kawashima Toyozo Takada Tetsuzo Kato 《Journal of heterocyclic chemistry》1985,22(2):569-574
Raney nickel hydrogenation of Z-3-aryl-5-(ethoxycarbonyl)methylene-5,6-dihydro-4H-1,2,4-oxadiazine ( 1a-c ) affords 2-aryl-6-hydroxymethyl-4-pyrimidinone ( 2 ) and ethyl (2-aryl-4-oxazolyl)acetate ( 3 ). A similar hydrogenation of Z-5-arylcarbarnoyl)methylene-5,6-dihydro-3-phenyl-4H-1,2,4-oxadiazine ( 1d-f ) gives E-4-(arylcarbamoyl)methylene-2-phenyl-2-oxazoline ( 5 ), 4-(arylcarbamoyl)methyl-2-phenyloxazole ( 6 ), and Z-4-(aryl-carbamoyl)methylene-2-phenyl-2-oxazoline ( 7 ). 相似文献
15.
John T. Shaw Robert J. Thomas Sherry A. Herold Gregory A. Gfesser Ralph A. Isovitsch 《Journal of heterocyclic chemistry》1991,28(8):1835-1836
The reaction of 2-amino-4-chloro-6-methylpyrimidine ( 3a ) with trimethylacetyl chloride gave 4-chloro-6-methyl-2-trimethylacetamidopyrimidine ( 5 ). This latter compound with excess anthranilonitrile gave in one step 2-t-butyl-5-methyl-1,3,4,7,11c-pentaazabenz[de]anthracene ( 6a ). To prepare 2-t-butyl-5-dimethylamino-1,3,4,6,7,11c-hexaazabenz[de]anthracene ( 6b ) it was found necessary to first react 2-amino-4-chloro-6-dimethylamino -5 -triazine ( 3b ) with anthranilonitrile to yield the intermediate product 2-amino-4(2-cyanoanilino)-6-dimethylamino-s-triazine ( 4 ). Reaction of the latter with trimethylacetyl chloride gave 6b . 相似文献
16.
Y. Tarumi Y. Takebayashi K. Moriguchi T. Atsumi T. Fukumaru H. Yamamoto 《Journal of heterocyclic chemistry》1980,17(7):1425-1433
Acylation of 4-carbamoylimidazolium-5-olate ( 2 ) with a variety of acid chlorides produced 4(5)-carbamoyl-1H-imidazol-5-(4)yl acid carboxylates ( 3a-j ). Treatment of esters 3a,c with sodium hydroxide gave imides, 4a,c . Methylation of 3a and 2 with diazomethane gave the N-3 methyl derivative ( 6 ) and a mixture of the N-3, O-dimethyl derivative ( 9 ), the N-1, N-3-dimethyl derivative ( 10 ) and the O-methyl derivative ( 11 ), respectively. 5-Carbamoyl-1-methylimidazolium-4-olate ( 7 ) and its 4-carbamoyl isomer ( 16 ) were prepared from 2-aminopropanediamides 8 and 15 , respectively. Treatment of the imidazolium compound ( 10 ) with aqueous potassium hydroxide gave the recyclized product, 1-methyl-5-methylcarbamoylimidazolium 4-olate ( 18 ). Methyl derivatives 6, 7 , and 9 except 16 demonstrated the complete lack of antitumor activity against Lewis lung carcinoma or sarcoma 180 in mice. 相似文献
17.
John T. Shaw Mallory F. Egler Victoria S. Peciulis Regina Pustover William G. Ruth 《Journal of heterocyclic chemistry》1990,27(6):1591-1595
The reaction of 7,9-dibromo-5-tribromomethyl-2-t-butyl-4-cyano-1,3,6,9b-tetraazaphenalene ( 1a ) with 2-amino-5-picoline is shown to give 4,6-dibromo-2-t-butyl-13-imino-11-methyl-13H-1,3,7,8,12a,13c-hexaazabenzo[de]naphthacene ( 3 ) and the isomeric 7,9-dibromo-2-t-butyl-4-cyano-5N-(5-methyl-2-pyridyl)amino-1,3,-6,9b-tetraazaphenalene ( 2a ). A related annulation reaction of 7,9-dibromo-2-t-butyl-5-chloro-4-cyano-1,3,6,9b-tetraazaphenalene ( 1g ) with 2-amino-6-trimethylacetamidopyridine leads in two steps to 4,6-dibromo-2,13-di-t-butyl-1,3,7,8,11b,12,14,14d-octaazadibenzo[de,hi]naphthacene ( 4a ). The preparation of 1g , 5-azido-7,9-dibromo-2-t-butyl-4-cyano-1,3,6,9b-tetraazaphenalene ( 1c ) and the reaction of the latter with pyrrolidine leading to 7,9-dibromo-2-t-butyl-4-cyano-5-(1-pyrrolidino)-1,3,6,9b-tetraazaphenalene ( 1e ) are also reported. Attempted displacement of the azido-group on 1c by 2,6-diaminopyridine affords surprisingly 5-amino-7,9-dibromo-2-t-butyl-4-cyano-1,3,6,9b-tetraazaphenalene ( 1d ). 相似文献
18.
Shunsaku Shiotani Youichi Tsukamoto Yasuyuki Kitagawa 《Journal of heterocyclic chemistry》1997,34(1):129-141
Furo[3,2-c]-( 1a ), -[2,3-c]- ( 1b ) and -[3,2-b]pyridine ( 1c ) were reacted with isopropyl chloroformate and trimethyl phosphite to give dimethyl 5-isopropoxycarbonyl-4,5-dihydrofuro[3,2-c]pyridine-4-phosphonate ( 2a ), dimethyl 6-isopropoxycarbonyl-6,7-dihydrofuro[2,3-c]pyridine-7-phosphonate ( 2b ) and dimethyl 4-isopropoxycarbonyl-4,7-dihydrofuro[3,2-b]pyridine-7-phosphonate ( 2c ) as unstable syrups. Reaction of 2b and 2c with n-butyllithium and then with benzaldehyde, p-methoxybenzaldehyde, p-cyanobenzalde-hyde or propionaldehyde afforded the normal Wittig reaction products 5b-H, 5b-OMe, 5b-CN, 5b-Et, 5c-H, 5c-H, 5c-OMe and 5c-CN , except for 2b with propionaldehyde. While, the same reactions of compound 2a and the reaction of 2b with propionaldehyde afforded the unexpected products, 5-isopropoxycar-bonylfuro[3,2-c]pyridinio-4-aryl-(or ethyl)methoxides 3a-H, 3a-OMe, 3a-CN and 3a-Et , 4-(1′-aryl(or ethyl)-1′-hydroxymethyl)furo[3,2-c]pyridines 4a-H, 4a-OMe, 4a-CN and 4a-Et accompanying formation of the normal products. Treatment of the normal Wittig reaction products with lithium diisopropylamide and then with acetone gave the derivatives alkylated at the 2-or the benzylic positions. 相似文献
19.
Mara E. F. Braibante Gunter Clar Marcos A. P. Martins 《Journal of heterocyclic chemistry》1993,30(4):1159-1160
1-Methyl-5-(trifluoromethyl)-1H-pyrazoles 2, 3 and 4,5-dihydro-1-phenyl-5-(trifluoromethyl)-1H-pyrazol-5-ol 4 were prepared by reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones 1 and hydrazine, methylhydrazine, and phenylhydrazine, respectively, in good yields. Compound 1 proved to be a versatile building block for the regiospecific construction of pyrazole rings having an 5-trifluoromethyl substituent. 相似文献
20.
Takushi Kurihara Masanobu Mori Yasuhiko Sakamoto 《Journal of heterocyclic chemistry》1977,14(3):523-525
Reaction of 3-(o-ehlorobenzylidene)-2,4-dioxopentanoic acid (1) with hydroxylamine hydro-chloride in acetic acid gave 5-(o-chlorophenyl)-3-methyl-4-(α-hydroxyimino)isoxazolineglyo-xylic acid (5) and 3-(o-chlorobenzylidene)-4-hydroxyimino-2-oxopentanoic acid (2) in 57% and 7% yields. Pyrolysis of 5 afforded 5-(o-chlorophenyl)-3-methylisoxazole-4-carbonitrile (8), cis- and trans-5-(o-chlorophenyl)-3-methylisoxazoline-4-carbonitriles (9,10), and 5-(o-chloro-phenyl)-3-methylisoxazoline-4-carboxamide (11). 相似文献