N. F. Kirillov

Reaction of Reformatsky reagent prepared from methyl 1-bromocyclohexanecarboxylate and zinc with substituted chalcones

Methyl 1-bromocyclohexanecarboxylate reacts with zinc and substituted chalcones yielding the corresponding spiro-3,4-dihydropyran-2-one derivatives, 3-aryl-5-aryl-2-oxaspiro[5.5]undec-3-en-1-ones.

Reaction of substituted chalcones with methyl 1-bromocycloalkanecarboxylates and zinc

Methyl 1-bromocyclopentane-and 1-bromocyclobutanecarboxylates react with zinc and substituted chalcones to form spiro-3,4-dihydropyran-2-one derivatives: 8, 10-diaryl-7-oxaspiro[4.5]dec-8-en-6-ones and 7,9-diaryl-6-oxaspiro[3.5]non-7-en-5-ones, respectively.

Reformatsky synthesis of 16-aryl-15-oxadispiro[5.1.5.3]-hexadecane-7, 14-diones

Methyl 1-bromocyclohexanecarboxylate reacts with zinc in the presence of cyclohexanecarbonyl chloride to give methyl 1-(cyclohexylcarbonyl)cyclohexanecarboxylate. Treatment of the latter with bromine leads to formation of methyl 1-(1-bromocyclohexylcarbonyl)cyclohexanecarboxylate which reacts with zinc and aromatic aldehydes, yielding 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones.

Synthesis and analgesic activity of 3,5-diaryl-2-oxaspiro[5,6]dodec-3-en-1-ones

3,5-Diaryl-2-oxaspiro[5,6]dodec-3-en-1-ones were prepared by the reaction of methyl-1-bromocycloheptane carboxylates with zinc and 1,3-diarylprop-2-en-1-ones. The synthesized compounds possessed analgesic activity and exhibited low toxicity.

Reaction of alicyclic reformatsky reagents with 2-arylmethylene-1,3-diphenylpropane-1,3-diones

Previously we found that the reaction of alicyclic Reformatsky reagents with 1,3-diarylprop-2-ene-1ones resulted in the substituted spirodihydropyranones [1, 2]. In continuation of these studies we examined the reaction of the Reformatsky reagents IIa and IIb derived from methyl 1-bromocycloalkylcarboxylates Ia and Ib and zinc with 2-arylmethylene-1,3-diphenylpropane-1,3-dione IIIa–IIIf. Our study showed that addition of the organozinc reagents IIa–IIb to the unsaturated diketones IIIa–IIIf occurs in 1,4-position to form the intermediates IVa–IVe, Va–Vf followed by the cyclization with the release of bromozinc methylate to form 10-aryl-9-benzoyl-8-phenyl-7-oxaspiro[4.5]dec-8-ene-6-ones VIa–VIf and 5-aryl-4benzoyl-3-phenyl-2-oxaspiro[5.5]undec-3-ene-1-ones VIIa–VIIf, respectively. DOI: 10.1134/S1070363211060302

Reaction of 1,5-diarylpenta-1,4-dien-3-ones with methyl 1-bromocycloalkanecarboxylates and zinc

Methyl 1-bromocyclopentane-, 1-bromocyclohexane- and 1-bromocycloheptanecarboxylates react with zinc and 1,5-diarylpenta-1,4-dien-3-ones to form 10-aryl-8-(2-arylethenyl)-7-oxaspiro[4.5]dec-8-en-6-ones, 5-aryl-3-(2-arylethenyl)-2-oxaspiro[5.5]undec-3-en-1-ones, and 5-aryl-3-(2-arylethenyl)-2-oxaspiro[5.6]-dodec-3-en-1-ones, respectively.

Synthesis of spiro- and dispirotetrahydropyrane-2,4-diones involving cyclobutane fragment in position 5 of heterocycle

Methyl 3-(1-bromocyclobutyl)-2,2-dimethyl-3-oxopropanoates, 1-(1-bromocyclobutyl-carbonyl) cyclopentanoates and 1-(1-bromocyclobutylcarbonyl)cyclobutanoates react with zinc and aromatic aldehydes to form 5-aryl-8,8-dimethyl-6-oxaspiro[3.5]nonane-7,9-diones, 13-aryl-12-oxadispiro[3.1.4.3]tridecane-5,11-diones and 12-aryl-11-oxadispiro[3.1.3.3]dodecane-5,10-diones respectively.

Study of reaction of reformatsky reagent prepared from methyl bromocyclopentanecarboxylate and zinc with 2-oxochromen-and 6-bromo-2-oxochromen-3-carboxylic acids N-arylamides

Reformatsky reagent prepared from methyl 1-bromocyclopentanecarboxylate and zinc reacted with 2-oxochromen-and 6-bromo-2-oxochromen-3-carboxylic acids N-arylamides yielding 3-aryl-1,1-tetramethylene-and 3-aryl-9-bromo-1,1-tetramethylene-2,3,4,4a,5,10b-hexahydro-1H-chromeno[3,4-c]pyridine-2,4,5-triones as single diastereomers.

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.

Synthesis of 14-Aryl-13-oxadispiro[3.1.5.3]tetradecane-5,12-diones by the reformatsky reaction

Methyl 1-bromocyclohexanecarboxylate reacts with zinc in the presence of cyclobutanecarbonyl chloride to give methyl 1-(cyclobutylcarbonyl)cyclohexanecarboxylate. Bromination of the latter leads to the formation of methyl 1-(1-bromocyclobutylcarbonyl)cyclohexanecarboxylate which reacts with zinc and aromatic aldehydes, yielding 14-aryl-13-oxadispiro[3.1.5.3]tetradecane-5,12-diones.