Five-membered 2,3-dioxo heterocycles: XCIII. Spiro heterocyclization of 4,5-diaroyl-1H-pyrrole-2,3-diones with acyclic enamine. Crystalline and molecular structure of substituted 1,7-diazaspiro[4.4]nonane

4,5-Diaroyl-1-aryl-1H-pyrrole-2,3-diones reacted with ethyl 3-amino-3-phenylprop-2-enoate to give ethyl 4-aroyl-1,6-diaryl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro[4.4]nona-3,6,8-triene-9-carboxylates. The crystalline and molecular structures of ethyl 4-benzoyl-3-hydroxy-1-(4-methylphenyl)-2-oxo-6,8-diphenyl-1,7-diazaspiro[4.4]nona-3,6,8-triene-9-carboxylate were determined by X-ray analysis.     

Five-membered 2,3-dioxo heterocycles: C. Reaction of methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carbocylates with acyclic enamines

Methyl 1-aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carbocylates react with N-substituted ethyl 3-amino-3-phenylprop-2-enoates, ethyl 3-aminobut-2-enoates, 3-amino-1,3-diphenylprop-2-en-1-ones, and dimethyl 2-arylaminofumarates to give 9-ethoxycarbonyl-, 9-benzoyl-, and 8,9-bis(methoxycarbonyl)-4-cinnamoyl-1,7-diazaspiro[4.4]nona-3,8-dienes.     

Five-membered 2,3-dioxo heterocycles: LXXII. Recyclization of isopropyl 2-(1-aryl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)-2-oxoacetates by the action of aliphatic amines

Reactions of isopropyl 2-(1-aryl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)-2-oxoacetates with alkylamines involve pyrroledione-pyrroledione recyclization with formation of isopropyl 1-aryl-2-hydroxy-4,5-dioxo-3-[phenyl(alkylamino)methylidene]pyrrolidine-2-carboxylates.     

Reactions of zinc enolates derived from 1-aryl-2-bromo-alkanones and 1-aryl-2-bromo-2-phenylethanone with 3-aroyl-6-bromochromen-2-ones and 2-benzoylbenzo[f]chromen-3-one

3-Aroyl-6-bromochromen-2-ones and 2-benzoylbenzo[f]chromen-3-one reacted with zinc enolates derived from 1-aryl-2-bromoalkanones and 1-aryl-2-bromo-2-phenylethanone to give, respectively, 4-(1-alkyl-2-aryl-2-oxoethyl)-3-aroyl-6-bromochroman-2-ones and 1-(2-aroyl-1-methyl-2-oxoethyl)-2-benzoyl-1,2-dihydrobenzo[f]chromen-3-ones as a single stereoisomer. Treatment with acetic anhydride of the intermediate product obtained from 3-benzoyl-6-bromochromen-2-one and [1-(4-chlorophenyl)-2-phenylethen-1-yloxy]-zinc(II) bromide resulted in the formation of 3-(1-acetoxy-1-phenylmethylidene)-6-bromo-4-[2-(4-chlorophenyl)-2-oxo-1-phenylethyl]chroman-2-one.     

Recyclization of 4,5-bis(aroyl)-2,3-dihydro-1H-pyrrole-2,3-diones by the action of aromatic amines

Russian Journal of Organic Chemistry -     

Reactions of bromine-containing organozinc compounds derived from α,α-dibromo ketones with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones

Bromine-containing organozinc compounds generated from 1,1-dibromo-3,3-dimethylbutan-2-one reacted with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones to give 3-aryl-2-(2,2-dimethylpropanoyl)spiro[cyclopropane-1,2′-indan]-1′,3′-diones and 1-aryl-6,6-dimethyl-2-(2,2-dimethylpropanoyl)-5,7-dioxaspiro[2.5]octan-4,8-diones, respectively. Reactions of 2-arylmethylideneindan-1,3-diones with bromine-containing zinc enolates derived from 1-aryl-2,2-dibromopropan-1-ones and 2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one resulted in the formation of 2-aroyl-3-aryl-2-methylspiro-[cyclopropane-1,2′-indan]-1′,3′-diones and 2,3: 8,9-dibenzo-12-phenyldispiro[4.0.5.1]dodecane-1,4,7-trione, respectively.     

Two directions in spiroheterocyclization of 1H-pyrrole-2,3-diones upon the action of 3-arylamino-1H-inden-1-ones

4-Ethoxycarbonyl-5-phenyl-substituted 1H-pyrrole-2,3-diones react with 3-arylamino-1H-inden-1-ones in the ratios 1: 1 and 1: 2 to form substituted spiro{indeno[1,2-b]quinoline-10,3??-pyrroles} and substituted spiro{diindeno[1,2-b:2??,1??-e]pyridine-11,3??-pyrroles}, respectively.     

Five-membered 2,3-dioxoheterocycles: LXXXVII. [4+2]-cycloaddition of alkyl vinyl ethers and 3,4-dihydro-2H-pyran to 4,5-diaroyl-1 H-pyrrole-2,3-diones

1-Aryl-4,5-diaroyl-1H-pyrrole-2,3-diones react with alkyl vinyl ethers and 3,4-dihydro-2H-pyran affording 1,4-diaryl-7a-aroyl-6-ethoxy-7,7a-dihydropyrano[4,3-b]pyrrole-2,3(1H,6H)-diones and 1,4-diaryl-9baroyl-1,7,8,9,9a-hexahydro-5aH-pyrano[3??,2??:5,6]pyrano[4,3-b]-pyrrole-2,3-diones respectively.     

Reformatsky reaction of methyl 1-bromocyclohexane-1-carboxylate with N-aryl-2-oxochromene-3-carboxamides

Reformatsky reagent generated from methyl 1-bromocyclohexane-1-carboxylate reacted with N-aryl-2-oxochromene-3-carboxamides and N-aryl-6-bromo-2-oxochromene-3-carboxamides to give, depending on the conditions, the corresponding N-aryl-(6-bromo)-4-(1-methoxycarbonylcyclohexyl)-2-oxochroman-3-carboxamides or 3-aryl-(9-bromo)-1,1-pentamethylene-2,3,4,4a,5,10b-hexahydro-1H-chromeno[3,4-c]pyridine-2,4,5-triones. The products were isolated as a single diastereoisomer.     

Reactions of zinc enolates derived from 1-aryl-2-bromo-2-phenylethanone and 2-bromoindan-1-one with alkyl 2-oxochromene-and 6-bromo-2-oxochromene-3-carboxylates

Zinc enolates derived from 1-aryl-2-bromo-2-phenylethanone react with alkyl 2-oxochromene-3-carboxylates and methyl 6-bromo-2-oxochromene-3-carboxylate to give, respectively, alkyl 4-(2-aryl-2-oxo-1-phenylethyl)-2-oxochroman-3-carboxylates and methyl 6-bromo-4-(2-aryl-2-oxo-1-phenylethyl)-2-oxochroman-3-carboxylate as a single stereoisomer. Zinc enolates derived from 2-bromoindan-1-one react with alkyl 2-oxochromene-3-carboxylates to give alkyl 2-oxo-4-(1-oxoindan-2-yl)chroman-3-carboxylates as a single stereoisomer.