Three-Component Spiro Heterocyclization of Pyrrolediones with Malononitrile and Cyclic Enols

Ethyl 4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates reacted with malononitrile and five-membered cyclic enols, indan-1,3-dione and cyclopentane-1,3-dione to give 1-substituted ethyl 2-amino-3- cyano-2′,5-dioxo-5′-phenyl-1′,2′-dihydro-5H-spiro[indeno[1,2-b]pyran-4,3′-pyrrole]-4′-carboxylates and ethyl 2-amino-3-cyano-2′,5-dioxo-5′-phenyl-1′,2′,6,7-tetrahydro-5H-spiro[cyclopenta[b]pyran-4,3′-pyrrole]-4′-carboxylates, respectively.     

Reaction of zinc enolates prepared from 2,2-dibromoindan-1-one or 2,2-dibromo-1-tetralone and zinc with 2-oxochromen-3-carboxylic acid derivatives

Zinc enolates obtained from 2,2-dibromonidan-1-one or 2,2-dibromo-1-tetralone and zinc reacted with alkyl esters and amides of 2-oxochromen-3-carboxylic acid giving the corresponding derivatives of 2,1′-dioxo-spiro(1a,7b-dihydrocyclopropa[c]chromen-1,2′-indan)-or 1′,2′,3′,4′-tetrahydro-2,1′-dioxospiro(1a,7b-dihydrocyclopropa[c]chromen-1,2′-naphthalene)-1a-carboxylic acids prevailingly in the form of a single geometric isomer.     

Five-membered 2,3-dioxoheterocycles: XC. Reaction of 4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-diones with enaminoesters. crystal and molecular structure of 4-methyl 9-ethyl 7-benzyl-3-hydroxy-8-methyl-1-(4-methoxyphenyl)-2,6-dioxo-1,7-diazaspiro[4.4]nona-3,8-diene-4,9-dicarboxylate

1-Aryl-4,5-bis(methoxycarbonyl)-1H-pyrrole-2,3-diones react with ethyl 3-(benzylamino)but-2-enoate and ethyl 3-(benzylamino)-3-phenylacrylate giving 4-methyl 9-ethyl 1-aryl-7-benzyl-3-hydroxy-8-methyl- and 4-methyl 9-ethyl 1-aryl-7-benzyl-3-hydroxy-8-phenyl-2,6-dioxo-1,7-diazaspiro[4.4]nona-3,8-diene-4,9-dicarboxylates.     

Five-membered 2,3-dioxo heterocycles: LXXXIX. Reaction of methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with (E)-4-arylaminopent-3-en-2-ones. Crystalline and molecular structure of 9-acetyl-4-cinnamoyl-3-hydroxy-1-(4-methoxyphenyl)-8-methyl-7-phenyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-dione

Methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 4-benzylamino- and 4-arylaminopent-3-en-2-ones to give 1-aryl-7-benzyl- and 1,7-diaryl-9-acetyl-4-cinnamoyl-3-hydroxy-8-methyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-diones. The crystalline and molecular structures of 9-acetyl-4-cinnamoyl-3-hydroxy-1-(4-methoxyphenyl)-8-methyl-7-phenyl-1,7-diazaspiro[4.4]nona-3,8-diene-2,6-dione were studied by X-ray analysis.     

Reaction of zinc enolates derived from 1-aryl-2,2-dibromoalkan-1-ones with 2-arylmethylidenemalononitriles

Zinc enolates derived from 1-aryl-2,2-dibromoalkan-1-ones react with 2-arylmethylidenemalononitriles to give 2-alkyl-3-aryl-2-aroylcyclopropane-1,1-dicarbonitriles.     

Recyclization of Pyrrolediones with Arylaminoindenones. Synthesis of Indeno[1,2-<Emphasis Type="Italic">b</Emphasis>]pyridines

Dimethyl 1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylates reacted with 3-arylamino-1H-inden-1-ones to give the corresponding methyl 1-aryl-3-[2-(arylamino)-2-oxoacetyl]-2,5-dioxo-2,5-dihydro-1H-indeno[1,2-b]pyridine-4-carboxylates.     

Reactions of organozinc reagents derived from dialkyl 2,2-dibromomalonates with 3-aryl-2-cyanoprop-2-enamides

Organozinc compounds obtained by treatment of dialkyl 2,2-dibromomalonates with metallic zinc reacted with N-substituted 3-aryl-2-cyanoprop-2-enoic acid amides to give alkyl 3-R-6-aryl-5-cyano-2,4-dioxo-3-azabicyclo[3.1.0]hexane-1-carboxamides as a single stereoisomer.     

Reactions of Zinc Enolates Formed from 1-Aryl-2-bromo-2-phenylethanone or 2-Bromoindanone and Zinc,with Dimethyl 2-(1-Arylmethylene)malonates

Zinc enolates formed from 1-aryl-2-bromo-2-phenylethanones and zinc react with dimethyl 2-(1-arylmethylene)malonates to afford dimethyl 2-(1,3-diaryl-3-oxo-2-phenylpropyl)malonates. The latter react with cyclohexylamine, piperidine, or morpholine to give the corresponding monosubstituted amides. The zinc enolate derived from 2-bromoindanone and zinc reacts with dimethyl 2-(4-bromobenzylidene)malonate, yielding dimethyl 2-[(4-bromophenyl)(1-oxoindan-2-yl)methyl]malonate. The final products largely form as a single diastereomer.