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1.
Alberto Bargagna Pietro Schenone Mario Longobardi 《Journal of heterocyclic chemistry》1986,23(4):1067-1070
1,4-Cycloaddition of phenylchloroketene to N,N-disubstituted 2-aminomethylene-3,4-dihydro-1(2H)naphthalenones gave the corresponding adducts, namely N,N-disubstituted 4-amino-3-chloro-3,4,5,6-tetrahydro-3-phenyl-2H-naphtho[1,2-b]pyran-2-ones II, in the case of aliphatic N,N-disubstitution or aromatic N-monosubstitution. Apart from IIf (NR2 = NMePh), adducts II were unstable and were dehydrochlorinated in situ with DBN to give N,N-disubstituted 4-amino-5,6-dihydro-3-phenyl-2H-naphtho[1,2-b]pyran-2-ones III in fair overall yields. Compounds III were dehydrogenated with Pd/C in boiling p-cymene to afford the title compounds generally in high yields. 相似文献
2.
Alberto Bargagna Pietro Schenone Filippo Evangelisti 《Journal of heterocyclic chemistry》1979,16(1):93-96
The dipolar 1,4-cycloaddition of dichloroketene to N,N-disubstituted 3-amino-1-phenyl-2-propene-1-onesled directly to N,N-disubstituted 4-amino-3-chloro-6-phenyl-2H-pyran-2-ones only in the case of an usual aliphatic N,N-disubstitution. In the case of partial or full aromatic N-substitution, N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-6-phenyl-2H-pyran-2-ones were instead obtained, which were dehydrochlorinated with DBN to the corresponding 4-amino-3-chloro-6-phenyl-2H-pyran-2-ones. 相似文献
3.
Cycloaddition of dichloroketene to N,N-disubstituted 6-aminomethylene-5,6-dihydro-2-phenylbenzothiazol-7-(4H)ones gave in good yield N,N-disubstituted 4-amino-3,3-dichloro-3,4,5,6-tetrahydro-8-phenyl-2H-pyrano[3,2-g]benzothiazol-2-ones II, which are derivatives of the new heterocyclic system 2H-pyrano[3,2-g]benzothiazole. Dehydrochlorination with triethylamine of II afforded N,N-disubstituted 4-amino-3-chloro-5,6-dihydro-8-phenyl-2H-pyrano[3,2-g]benzothiazol-2-ones III in good to moderate yield. The dimethylamino adduct was dehydrochlorinated in high yield by refluxing in toluene, whereas the diisopropylamino adduct gave in low yield 6-(2,2-dichloroethylidene)-5,6-dihydro-2-phenylbenzothiazol-7-(4H)one with the triethylamine treatment. The dehydrochlorinated product IIId (NR2 = pyrrolidino) was obtained directly in low yield by cycloaddition of dichloroketene to the corresponding enaminone. Full aromatisation of IIIa,g [NR2 = N(CH3)2 and N(CH3)C6H5, respectively] to the corresponding N,N-disubstituted 4-amino-3-chloro-8-phenyl-2H-pyrano-[3,2-g]benzothiazol-2-ones was accomplished with DDQ in refluxing benzene. 相似文献
4.
The 1,4-cycloaddition of sulfene to N,N-disubstituted 5-aminomethylene-1,5,6,7-tetrahydro-2-methyl-1-phenylindol-4-ones afforded N,N-disubstituted 3,4,5,6-tetrahydro-8-methyl-7-phenyl-7H-1,2-oxathiino[6,5-e]indol-4-amine 2,2-dioxides only in the case of aliphatic N-substitution. The 1,4-cycloaddition of dichloroketene occurred normally only in the case of 1,5,6,7-tetrahydro-2-methyl-1-phenyl-5-piperidinomethyleneindol-4-one to give 3,3-dichloro-3,4,5,6-tetrahydro-8-methyl-7-phenyl-4-piperidino-7H-pyrano[2,3-e]indol-4-one. Attempted recrystallisation, dehydro-chlorination or treatment with palladium on carbon of this adduct, as well as reaction of similar enaminoketones with dichloroketene, gave instead the same product, namely 3-chloro-8-methyl-7-phenyl-7H-pyrano[2,3-e]indol-4-one, as a result of dehydrochlorination, dehydrogenation and subsequent hydrogenolysis of the C-NR2 bond in the primary adduct. 相似文献
5.
The dipolar 1,4-cycloaddition of dichloroketerie to N,N-disubslituled 3-aminomethylene-2,3-dihydro-4-thiochromanones and 3-aminomethylenetelrahydro-4-thiopyranones gave N,N-disubstituted 4-amino-3,3-diehloro-3,4-dihydro-2H,5H-[1]benzolhiopyrano[4,3-b]pyran-2-ones and 4-amino-3,3-dichloro-3,4,7,8-tetrahydro-2H,5H-thiopyrano[4,3-b]pyran-2-ones, respectively, only in the ease of aromatic or strong hindering aliphatic N-substitution. The adducts gave N,N′-disubstituted 4-amino-3-chloro-2H,5H-[1]benzothiopyrano[4,3-b]pyran-2-ones and 4-amino-3-chloro-7,8-dihydro-2H,5H-thiopyrano[4,3-b]pyran-2-ones, respectively, by dehydro-chlorination with DBN. By chromatography on neutral alumina, 3-(2,2-dichloroethylidene)-2,3-dihydro-4-thiochromanone was isolated as an unstable liquid from the reaction between dichloroketerie and 3-diethylaminornethylene-2,3-dihydro-4-thiochromanone. 相似文献
6.
Alberto Bargagna Filippo Evangelisti Pietro Schenone 《Journal of heterocyclic chemistry》1981,18(1):111-116
Cycloaddition of sulfene to N,N-disubstituted 4-amino-3-phenyl-3-buten-2-ones (III) occurred in good yield only in the case of aliphatic N-substitution to give 4-dialkylamino-3,4-dihydro-6-methyl-5-phenyl-1,2-oxathiin 2,2-dioxides, whereas N,N-disubstituted 4-amino-1-phenyl-3-buten-2-ones (IV) did not react at all. Polar 1,4-cycloaddition of dichloroketene to III and IV occurred partly in the case of aromatic N-substitution, with the exception of the morpholino derivative IVd, giving in low yield N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-(6-methyl-5-phenyl)(6-benzyl)-2H-pyran-2-ones, which were dehydrochlorinated with DBN to the corresponding 4-amino-3-chloro-(6-methyl-5-phenyl)(6-benzyl)-2H-pyran-2-ones (VII) in good yield. In some cases of aliphatic N,N-disubstitution of III and IV, cycloaddition led directly to N,N-dialkyl derivatives VII in low yield. 相似文献
7.
Alberto Bargagna Pietro Schenone Francesco Bondavalli Mario Longobardi 《Journal of heterocyclic chemistry》1982,19(2):257-261
Cycloaddition of dichloroketene to N,N-disubstituted (E)-amino-5-methyl-1,4-hexadien-3-ones IV and (E,E)-1-amino-5-phenyl-1,4-pentadien-3-ones V occurred in moderate to good yield only in the case of aromatic N-substitution to give N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-6-(2-methyl-l-propenyl) (2-phenylethenyl)-2H-pyran-2-ones, which were dehydrochlorinated with DBN to afford in good yield N,N-disubstituted 4-amino-3-chloro-6-(2-methyl-propenyl)(2-phenylethenyl)-2H-pyran-2-ones. In the case of aliphatic N,N-disubstitution (dimethylamino group) of enaminones IV and V, the Cycloaddition led directly in low yield to 3-chloro-4-dimethylamino-6-(2-methyl-l-propenyl)(2-phenylethenyl)-2H-pyran-2-ones. 相似文献
8.
Alberto Bargagna Sergio Cafaggi Pietro Schenone 《Journal of heterocyclic chemistry》1980,17(3):507-511
Cycloaddition of dichloroketene to N,N-disubstituted 1-amino-4-methyl-1-penten-3-ones and 1-amino-4,4-dimethyl-1-penten-3-ones occurred in moderate to fair yield only in the case of aromatic N-substitution to give N,N-disubstituted 6-alkyl-4-amino-3,3-dichloro-3,4-dihydro-2H-pyran-2-ones, which were dehydrochlorinated with DBN to afford in good yield N,N-disubstituted 6-alkyl-4-amino-3-chloro-2H-pyran-2-ones. In the case of aliphatic N,N-disubstitution, cyclo-addition led directly to 6-alkyl-4-dialkylamino-3-chloro-2H-pyran-2-ones only for N,N-disubstituted 1-amino-4,4-dimethyl-1-penten-3-ones. The reaction between 1-dimethylamino-4-methyl-1-penten-3-one and dichloroketene gave 3-chloro-4-dimethylamino-3,6-dihydro-6-isopropylidene-2H-pyran-2-one in low yield. 相似文献
9.
Alberto Bargagna Pietro Schenone Francesco Bondavalli Mario Longobardi 《Journal of heterocyclic chemistry》1980,17(6):1201-1206
Cycloaddition of sulfene to N,N-disubstituted 3-amino-2-methyl-1-phenyl-2-propen-1-ones (I) and 3-amino-1,2-diphenyl-2-propen-1-ones (II) occurred in good to moderate yield only in the case of aliphatic N-substitution to give 4-dialkylamino-3,4-dihydro-(5-methyl-6-phenyl)(5,6-diphenyl)-1,2-oxathiin 2,2-dioxides. Polar 1,4-cycloaddition of dichloroketene to I and II occurred only in the former case, giving in good to moderate yield N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-5-methyl-6-phenyl-2H-pyran-2-ones which were dehydrochlorinated with DBN to N,N-disubstituted 4-amino-3-chloro-5-methyl-6-phenyl-2H-pyran-2-ones. In the reaction of 2-methyl-1-phenyl-3-diphenylamino-2-propen-1-one with dichloroketene, a product was isolated which was proven by uv, ir, nmr and chemical evidence to be the dipolar ion VI, the supposed intermediate of the polar 1,4-cycloaddition of dichloroketene to N,N-disubstituted enaminones. 相似文献
10.
1,4-Cycloaddition of dichloroketene to a number of N,N-disubstituted (E)-4-amino methylene-3,4-dihydro-[1]benzothiepin-5(2H)-ones gave in excellent yield N,N-disubstituted 4-amino-3,3-dichloro-3,4,5,6-tetrahydro-2H-[1]benzothiepino[5,4-b]pyran-2-ones III, which are derivatives of the 2H-[1]benzothiepino[5,4-b]pyran system. Dehydrochlorination of III with DBN afforded N,N-disubstituted 4-amino-3-chloro-5,6-dihydro-2H-[1]-benzothiepino[5,4-b]pyran-2-ones, generally in excellent yield. 相似文献
11.
Cycloaddition of dichloroketene to N,N-disubstituted 3-aminomethylene-4-chromanones gave in good yield N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-5H-pyrano[3,2-c][1]benzopyran-2-ones only in the case of aromatic N-substitution. Dehydrochlorination with triethylamine of these adducts afforded N,N-disubstituted 4-amino-3-chloro-5H-pyrano[3,2-c][1]benzopyran-2-ones in good to moderate yield. The cycloaddition to 3-dimethylaminomethylene-4-chromanone led directly to 3-chloro-4-dimethylamino-5H-pyrano[3,2-c][1]benzopyran-2-one. 相似文献
12.
Cycloaddition of dichloroketone to N,N-disubstituted (E)-4-aminomethylene-3,4-dihydro-1-benzoxepin-5(2H)-ones gave N,N-disubstituted 4-amino-3,3-dichloro-3,4,5,6-tetrahydro-2H-pyrano[3,2-d]-1-benzoxepin-2-ones II, which are derivatives of the new heterocyclic system 2H-pyrano[3,2-d]-1-benzoxepin. Dehydrochlorination with triethylamine of II afforded N,N-disubstituted 4-amino-3-chloro-5,6-dihydro-2H-pyrano-[3,2-d]-1-benzoxepin-2-ones III in good to moderate yields. In the triethylamine treatment of IIh (NR2 = diphenylamino), 3-chloro-5,6-dihydro-2H-pyrano[3,2-d]-1-benzoxepin-2-one was isolated in low yield near to IIIh, whereas IIc (NR2 = diisopropylamino) gave in low yield 4-diisopropylamino-5,6-dihydro-2H-pyrano(3,2-d)-1-benzoxepin-2-one. 相似文献
13.
The polar 1,4-cycloaddition of dichloroketene to N,N-disubstituted (E)-5-aminomethylene-1,5,6,7-tetrahydro-(1-methyl)(1-phenyl)-4H-indazol-4-ones V, prepared from 1,5,6,7-tetrahydro-(1-methyl)(1-phenyl)-4H-indazol-4-ones via the 5-hydroxymethylene derivatives, gave in good yield N,N-disubstituted 4-amino-3,3-dichloro-4,5,6,7-tetrahydro-(7-methyl)(7-phenyl)pyrano[2,3-e]indazol-(3H)ones VI, which are derivatives of the new heterocyclic system pyrano[2,3-e]indazole. Dehydrochlorination of VI with DBN afforded N,N-disubstituted 4-amino-3-chloro-6,7-dihydro(7-methyl)(7-phenyl)pyrano[2,3-e]indazol-2(5H]-ones VII generally in satisfactory yield. Full aromatization with DDQ of VII was tried only in the case of dimethylamino derivatives, giving a moderate yield of 3-chloro-4-dimethylamino(7-methyl)(7-phenyl)pyrano[2,3-e]indazol-2(7H)-ones. Cycloaddition of sulfene to V occurred only in the case of aliphatic N-substitution to give in moderate yield 4-dialkylamino-4,5,6,7-tetrahydro-(7-methyl)(7-phenyl)-3H-1,2-oxathiino[6,5-e]indazole 2,2-dioxides, which are derivatives of the new heterocyclic system 1,2-oxathiino[6,5-e]indazole. 相似文献
14.
Luisa Mosti Pietro Schenone Giulia Menozzi Giovanni Romussi 《Journal of heterocyclic chemistry》1982,19(5):1057-1059
The polar 1,4-cycloaddition of sulfene to N,N-disubstituted (E)5-aminomethylene-6,7-dihydrobenzo[b]-thiophen-4(5H)ones II gave in excellent yield and only in the case of aliphatic N-substitution, N,N-disubstituted 4-amino-3,4,5,6-tetrahydrothieno[2,3-h]-1,2-benzoxathiin 2,2-dioxides III, which are derivatives of the new heterocyclic system thieno[2,3-h]-1,2-benzoxathiin. Dehydrogenation with DDQ of cycloadducts IIIa-d was successful only in the case of IIIa (NR2 = dimethylamino) to give in low yield 4-dimethylamino-3,4-dihydrothieno[2,3-h]-1,2-benzoxathiin 2,2-dioxide. 相似文献
15.
Giulia Menozzi Alberto Bargagna Luisa Mosti Pietro Schenone 《Journal of heterocyclic chemistry》1987,24(3):633-635
The 1,4-cycloaddition of sulfene to N,N-disubstituted (E)-6-aminomethylene-7,8-dihydro-(2-methyl)-(2-phenyl)quinazolin-5(6H)-ones I gave N,N-disubstituted 4-amino-3,4,5,6-tetrahydro-(8-methyl) (8-phenyl)-1,2-oxathiino[6,5-f]quinazoline 2,2-dioxides II , which are derivatives of the new heterocyclic system 1,2-oxathiino[6,5-f]quinazoline. With 2-phenylenaminones Id-h , the cycloaddition occurred, generally in satisfactory yields, both in the case of aliphatic N,N-disubstitution and aromatic N-monosubstitution, whereas with 2-methyl enaminones Ia-c the reaction took place in low yields only in the case of aliphatic N,N-disubstitution. Also the reaction of 2-phenyl enaminones Id-g with chlorosulfene occurred as with sulfene, giving a mixture of cycloadducts which were dehydrochlorinated in situ with DBN to afford N,N-di-substituted 4-amino-5,6-dihydro-8-phenyl-1,2-oxathiino[6,5-f]quinazoline 2,2-dioxides III generally in satisfactory yields. Compounds III could not be dehydrogenated either by DDQ in boiling benzene or by palladium on carbon in boiling p-cymene. 相似文献
16.
Luisa Mosti Pietro Schenone Giulia Menozzi Giovanni Romussi Francarosa Baccichetti 《Journal of heterocyclic chemistry》1982,19(5):1227-1229
Cycloaddition of sulfene to N,N-disubstituted (E)5-aminomethylene-6,7-dihydrobenzo[b]furan-4(5H)ones I gave, only in the case of aliphatic N-substitution and generally in satisfactory yields, N,N-disubstituted 4-amino-3,4,5,6-tetrahydrofuro[2,3-h]-1,2-benzoxathiin 2,2-dioxides II, which are derivatives of the new heterocyclic system furo[2,3-h]-1,2-benzoxathiin. The 4-dimethylamino and 4-piperidino cycloadducts IIa,e were dehydrogenated with DDQ to the corresponding 4-dialkylamino-3,4-dihydrofuro[2,3-h]-1,2-benzoxathiin 2,2-dioxides IIIa,e in low yield. Compounds IIIa,e were tested for photobiological activity and found to be inactive. 相似文献
17.
Gaetano Bignardi Luisa Mosti Pietro Schenone Giulia Menozzi 《Journal of heterocyclic chemistry》1977,14(6):1023-1028
The 1,4-cycloaddition of dichloroketene to N,N-disubstituted 6-aminomethylene-b,7,8,9-tetra-hydro-5H-benzocyclohepten-5-ones afforded N,N-disubstituted 4-amino-3,3-dichloro-3,4,6,7-tetrahydro-5H-benzo[3,4]cyclohepta[2,l-b]pyran-2-ones only in the case of aromatic or strong hindering aliphatic N-substitution. The adducts gave N,N-disubstituted 4-amino-3-chloro-b,7-dihydro-5H-benzo[3,4]cyclohepta[2,l-b]pyran-2-ones by dehydrochlorination with collidine. Upon chromatography on neutral alumina, two products were instead isolated in the case of usual aliphatic N-substitution (diethylamine, piperidine), namely 6-(2,2-dichloroethylidene)-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one and the dehydrochlorinated 2-pyrone; this latter was the sole product in the case of pyrrolidine substitution. The 1,4-cycloaddition of sulfene occurred readily to give N,N-disubstituted 4-amino-3,4,6,7-tetrahydro-5H-benzo[3,4]cyclohepta-[1,2-e]-1,2-oxathiin 2,2-dioxidesin the case of both aliphatic and partially aromatic N-substitution. 相似文献
18.
Reaction of sulfene with N,N-disubstituted 3-aminomethylene-1-(methyl, methylphenyl, phenyl)-4-piprridones and 3-aminomethylene-2,3-dihydro-1-plumy 1–4(1H) quinolones gave N,N-disubstituted 4-amino-3,4,5,6,7.8-hexahydro-6-(methyl, methylphenyl, phenyl)-1,2-oxathiino-[5,6-c] pyridine 2,2-dioxides and 4-amino-6-phenyl-3,4,5,6-tetrahydro-1,2-oxathiino[5,6-c]quinoline 2,2-dioxides, respectively, whereas N,N-disubstituted 3-aminomethylene-2,3-dihydro-1-methyl-4(1H) quinolones did not react. Slow air oxidation in the cold of intermediates 2,3-dihydro-3-hydroymethyIene-1-(methyl, phenyl)-4(1H) quinolones gave the corresponding 1-substituted 1,4-dihydro-4-oxo-3-quinolinecarboxyaldehydes. 相似文献
19.
Filippo Evangelisti Pietro Schenone Alberto Bargagna 《Journal of heterocyclic chemistry》1979,16(2):217-220
The title compounds were obtained by cycloaddition of sulfene to N,N-disubstituted 3-amino-1-phenyl-2-propen-1-ones and to 2-metbylphenylaminomethylenecycloalkanones, respectively. Steric and electronic aspects of these reactions, as well as the failure of cycloaddition in the case of N,N-disubstituted 4-arnino-3-buten-2-ones, are also discussed. 相似文献
20.
Filippo Evangelisti Gaetano Bignardi Alberto Bargagna Pietro Schenone 《Journal of heterocyclic chemistry》1978,15(3):511-512
The title compounds were obtained by dehydrochlorination with collidine, DBN or triethyl-amine of N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-5,6-polymethylene-2H-pyran-2-ones already described. 相似文献