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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 Gaetano Bignardi Pietro Schenone Mario Longobardi 《Journal of heterocyclic chemistry》1983,20(4):839-843
The polar 1, 4-cycloaddition of phenylsulfene (generated in situ from phenylmethanesulfony] chloride and triethylamine) to N, N-disubstituted (E)-2-aminomethylenecyclohexanones I gave in general a mixture of N, N-disubstituted cis- and trans-4-amino-3, 4, 5, 6, 7, 8-hexahydro-3-phenyl-1, 2-benzoxathiin 2, 2-dioxides III and IV, which were separated by column chromatography and whose structural and conformational features were determined from uv, ir and nmr spectral data. In the case of N, N-diisopropylamino enaminone 1c, the cyclo-addition took place with elimination of an alkyl group as propene to give the adduct III?. 相似文献
3.
Alberto Bargagna Pietro Schenone Gaetano Bignardi Mario Longobardi 《Journal of heterocyclic chemistry》1983,20(6):1549-1552
The polar 1,4-cycloaddition of chlorosulfene (generated in situ from chloromethanesulfonyl chloride and triethylamine) to N,N-disubstituted (E)-2-aminomethylenecyclohexanones I gave mixtures of N,N-disubstituted cis and trans 4-amino-3-chloro-3,4,5,6,7,8-hexahydro-1,2-benzoxathiin 2,2-dioxides III and IV, except for N,N-diphenyl enaminone which did not react. Only compounds IV could be separated from these mixtures by silica gel chromatography, with the exception of the piperidino adducts (III + IV)d, from which also IIId could be obtained pure. Compounds IV or mixtures III + IV were dehydrochlorinated with DBN in refluxing benzene to afford N,N-disubstituted 4-amino-5,6,7,8-tetrahydro-1,2-benzoxathiin 2,2-dioxides V in satisfactory yields. Structural and conformational features of compounds III, IV and V were determined from uv, ir and nmr spectral data. 相似文献
4.
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
5.
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
6.
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
7.
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
8.
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
9.
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
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 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
12.
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
13.
Luisa Mosti Pietro Schenone Giulia Menozzi Fernando Sancassan Francarosa Baccichetti Franco Benetollo Gabriella Bombieri 《Journal of heterocyclic chemistry》1988,25(2):407-413
1,4-Cycloaddition of phenylchloroketene to N,N-disubstituted 5-aminomethylene-6,7-dihydrobenzo[b]- furan-4(5H)-ones gave the corresponding adducts, namely N,N-disubstituted 4-amino-3-chloro-3,4,5,6-tetra- hydro-3-phenyl-2H-furo[2,3-h]-l-benzopyran-2-ones II , which were dehydrochlorinated with DBN to N,N-disubstituted 4-amino-5,6-dihydro-3-phenyl-2H-furo[2,3-h]-1-benzopyran-2-ones III . Compounds III afforded the title compounds IV by dehydrogenation with DDQ. In the cycloaddition step, 3-phenylangelicin V , whose structure was confirmed by 1H-nmr shift reagents data and by X-ray crystal structure determination, was almost always formed, probably starting from II by dehydrochlorination, dehydrogenation and hydrogenolysis of the disubstituted amino group. Separation of V was achieved by alumina chromatography either in the cycloaddition step or, in most cases, in the dehydrochlorination step. 3-Phenylangelicin crystallizes in the trigonal system, space group R3, with cell parameters (hexagonal axes) a = b = 41.021(10), c = 3.888(2) Å. The angelicin moiety forms a dihedral angle of 42.1(1)° with the phenyl substituent. Disordered solvent molecules of ethyl acetate are clathrated in channels in the direction of the crystallographic axis c. 相似文献
14.
Alberto Bargagna Pietro Schenone Francesco Bondavalli Mario Longobardi 《Journal of heterocyclic chemistry》1980,17(1):33-37
Cycloaddition of sulfene to N,N-disubstituted 4-amino-3-methyl-3-buten-2-ones (III) occurred in fair to good yield only in the case of aliphatic N-substitution to give 4-dialkylamino-3,4-dihydro-5,6-dimethyl-1,2-oxathiin 2,2-dioxides, whereas N,N-disubstituted 1-amino-1-penten-3-ones (II) did not react at all. Cycloaddition of dichloroketene to II, III and N,N-disubstituted 4-amino-3-buten-2-ones occurred only in the case of the methylphenylamino derivative, giving in good to moderate yield 6,(5)(di)alkyl-3,3-dichloro-3,4-dihydro-4-methylphenylamino-2-Hpyran-2-ones, which were dehydrochlorinated with DBN to 6,(5)(di)alkyl-3-chloro-4-methylphenylamino-2H-pyran-2-ones. 相似文献
15.
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
16.
Giulia Menozzi Alberto Bargagna Luisa Mosti Pietro Schenone 《Journal of heterocyclic chemistry》1986,23(2):455-458
The 1,4-cycloaddition of sulfene to N,N-disubstituted (E)-4-aminomethylene-3,4-dihydro[1]benzothiepin-5(2H)-ones I occurred only in the case of aliphatic N,N-disubstitution to give in good yield 4-dialkylamino-3,4,5,6-tetrahydro[1]benzothiepino[4,5-e][1,2]oxathiin 2,2-dioxides, which are derivatives of the new heterocyclic system [1]benzothiepino[4,5-e][1,2]oxathiin. Also the reaction of I with chlorosulfene occurred only in the case of aliphatic N,N-disubstitution to afford chiefly trans-4-dialkylamino-3-chloro-3,4,5,6-tetrahydro-[1]benzothiepino[4,5-e][1,2]oxathiin 2,2-dioxides III in satisfactory yield. Adducts III were dehydrochlorinated with DBN to 4-dialkylamino-5,6-dihydro[1]benzothiepino[4,5-e][1,2]oxathiin 2,2-dioxides in good yield. 相似文献
17.
Luisa Mosti Pietro Schenone Giulia Menozzi Sergio Cafaggi 《Journal of heterocyclic chemistry》1982,19(5):1031-1034
The polar 1,4-cycloaddition of sulfene to N,N-disubstituted 5-aminomethylene-1,5,6,7-tetrahydro-1-methylindol-4-ones occurred only in the case of aliphatic N-substitution to give, generally in good yield, 4-dialkylamino-3,4,5,6-tetrahydro-7-methyl-7H-1,2-oxathiino[6,5-e]indole 2,2-dioxides IV. Full aromatization of IVa (4-NR2 = dimethylamino) with DDQ in refluxing benzene gave in low yield 7-methyl-7H-1,2-oxathiino-[6,5-e]indole 2,2-dioxide, whereas the same reaction of IVe (4-NR2 = morpholinyl) with excess DDQ afforded in low yield 7-methyl-4-morpholinyl-7H-1,2-oxathiino[6,5-e]indole 2,2-dioxide. 相似文献
18.
The polar 1,4-cycloaddition of sulfene to N,N-disubstituted 6-aminomethylene-5,6-dihydro-2-phenylbenzothiazol-7-(4H)ones gave, generally in good yield, N,N-disubstituted 3,4,5,6-tetrahydro-8-phenyl-1,2-oxathiino-[5,6-g]benzothiazol-4-amine 2,2-dioxides, which are derivatives of the new heterocyclic system 1,2-oxathiino-[5,6-g]benzothiazole. This reaction did not occur only with the N,N-diphenylenaminone. 相似文献
19.
Giulia Menozzi Luisa Mosti Pietro Schenone Sergio Cafaggi 《Journal of heterocyclic chemistry》1982,19(4):937-939
The 1,4-cycloaddition of sulfene to N,N-disubstituted (E)-4-aminomethylene-3,4-dihydro-1-benzoxepin-5(2H)-ones gave, generally in excellent yield, N,N-disubstituted 4-amino-3,4,5,6-tetrahydro-1,2-oxathiino-[5,6-d)-1-benzoxepin 2,2-dioxides, which are derivatives of the new heterocyclic system 1,2-oxathiino[5,6-d]-1-benzoxepin. This reaction did not occur only with the N,N-diphenylenaminone. 相似文献
20.
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