F. S. Pashkovskii

Heterocyclic analogs of prostaglandines: IV. Synthesis of 3,7-interphenylene 3,10(11)-dioxa-13-azaprostanoids and 9-oxa-7-azaprostanoids based on tetronic acid and aromatic aldehydes

An approach was developed to the synthesis of stable in metabolism 3,7-interphenylene 3,10-dioxa-13-aza-and 3,11-dioxa-13-azaprostanoids, and also 9-oxa-7-azaprostanoids with interphenylene and terminal phenyl fragments in the ω-chain based on 3-(alkoxybenzylidene)-and 3-(3-phenylallylidene)tetrahydrofuran-2,4-diones obtained by Knoevenagel condensation of tetronic acid with alkoxy-substituted aromatic aldehydes and cinnamic aldehyde.

Tetronic acid in reaction with aromatic aldehydes and 2-naphthylamine. Investigation of fluorescent and nonlinear-optical characteristics of compounds obtained

By Knoevenagel condensation and by three-component condensation 3-arylmethylenetetrahydrofuran-2,4-diones and previously unknown 8,11-dihydro-11-arylbenzo[f]furo[3,4-b]quinolin-10(7H)-ones were respectively synthesized. The luminescent spectra and nonlinear-optical characteristics of compounds obtained were investigated.

Heterocyclic Analogs of Prostaglandins: I. Synthesis of 3-Alkyl(Aralkyl)-2,5-dihydrofuran-2-ones as Synthons for 11-Deoxy-10-oxaprostanoids

Abstract3-Acyl(arylmethyleneacyl)tetronic acids were synthesized. Selective hydrogenation of the carbonyl group in the acyl fragment and reduction of the conjugated double bond afforded in high yield the corresponding 3-alkyl(aralkyl) derivatives possessing either natural or modified prostaglandin α-chain. Reduction of the conjugated double bond in vinylogous 3-alkyl(aralkyl)tetronic acid amides with sodium cyanotrihydridoborate gave a mixture of stereoisomeric β-amino lactones which underwent retro-Michael elimination of the amine residue, leading to 3-alkyl(aralkyl)-2,5-dihydrofuran-2-ones. The latter can be regarded as synthons for 11-deoxy-10-oxaprostanoids.

Synthesis of benzo[f]quinoline derivatives by three-component condensation of tetronic acid with naphthalen-2-amine and formaldehyde

New derivatives of benzo[f]furo[3,4-b]quinoline, spiro[benzo[f]quinoline-2,3′-furan], and benzo[f]-quinoline-2-carboxylic acid were synthesized with high selectivity by three-component condensation of tetronic acid with naphthalen-2-amine and formaldehyde.

Heterocyclic analogs of prostaglandins: III*. Synthesis of 10-oxa-13-aza, 11-oxa-13-aza, and 9-oxa-7-aza prostanoids from 3-acyl- and 3-(3-arylprop-2-enoyl)furan-2,4-diones

A number of new 10-oxa-13-aza, 11-oxa-13-aza, and 9-oxa-7-aza prostanoids belonging to the B series were synthesized on the basis of 3-acyl-and 3-(3-arylprop-2-enoyl)furan-2,4(3H,5H)-diones. The scheme of synthesis includes selective hydrogenation of the exocyclic carbonyl group and reduction of the conjugated double bond in the acyl fragment of 3-acyl-and 3-(3-arylprop-2-enoyl)furan-2,4(3H,5H)-diones to obtain 3-alkyl-and 3-(3-arylpropyl)furan-2,4(3H,5H)-diones, transformation of the latter into the corresponding regioisomeric enol ethers via regioselective O-alkylation, and treatment of the enol ethers with primary aliphatic amines.

Heterocyclic analogs of prostaglandins: II. Synthesis of 10-oxaprostanoids with isoxazole and isoxazoline fragments in α-and ω-chain

By the use of “nitrile oxide procedure” from 3-alkyl(arylalkyl)-substituted 2,5-dihydro-2-furanones new 10-oxaprostanoids were prepared containing an isoxazole (isoxazoline) fragment in the α-or ω-prostanoid chain.

6,6-Heptamethylenetetrahydropyran-2,4-dione in the Synthesis of Benzo[f]pyrano[3,4-b]quinolines and Pyrano[4,3-b][4,7]phenanthrolines

Three-component condensation of 6,6-heptamethylenetetrahydropyran-2,4-dione with 2-amino-naphthalene or 6-aminoquinoline and aromatic aldehydes in an aliphatic alcohol afforded 12-aryl-9,9-hepta-methylene-8,9,10,12-tetrahydro-7H-benzo[f]pyrano[3,4-b]quinolin-11-ones and 12-aryl-9,9-heptamethylene-8,9,10,12-tetrahydro-7H-pyrano[4,3-b][4,7]phenanthrolin-11-ones, new N,O-heterocycles which include azaor diazaphenanthrene system fused to α-pyrone ring and aromatic and spiro substituents.

Tetrahydropyran-2,4-diones in the synthesis of fused N, O-heterocycles

Condensation of 6-methyl(or phenyl)-tetrahydropyran-2,4-diones with 2-aminonaphthalene or 6-aminoquinoline and aromatic aldehydes in an aliphatic alcohol gave 5-aryl-2,2-dimethyl(or 2-phenyl)-1,2,5,6-tetrahydro-4H-benzo[f]pyrano[3,4-c]quinolin-4-ones and 5-aryl-2-methyl-1,2,5,6-tetrahydro-4H-pyrano[4,3-a][4,7]phenanthrolin-4-ones which are new N,O-heterocyclic systems containing fused aza- and diazaphenanthrene moieties and a 2-pyranone ring.

Synthesis of (4-arylpyrrolidin-2-ylidene) derivatives of cyclic β-dicarbonyl compounds from cinnamoyl precursors

Abstract1,4-Conjugate Michael addition of nitromethane to the enone fragment of cinnamoyl derivatives of carbo- and heterocyclic β-dicarbonyl compounds provided the corresponding nitromethyl derivatives. The chemoselective reduction of the nitro group in the latter afforded 4-arylpyrrolidin-2-ylidene derivatives of β-dicarbonyl compounds in high yield. The reaction products with the heterocyclic β-dicarbonyl fragment are formed as equilibrium mixture of E- and Z-rotamers in which the E-rotamer predominates.

Chemical Transformations of 5,5-Dimethyl-2-(3-aryl-4-nitrobutanoyl)cyclohexane-1,3-diones. Synthesis of 6,7-Dihydrobenzo[d]isoxazol-4(5H)-ones and 6,7-Dihydro-1H-indazol-4(5H)-ones with Isoxazole and Isoxazoline Fragments in the Side Chain

By reaction of 5,5-dimethyl-2-(3-aryl-4-nitrobutanoyl)cyclohexane-1,3-diones with hydroxylamine and hydrazine hydrate 6,7-dihydrobenzo[d]isoxazol-4(5H)-ones and 6,7-dihydro-1H-indazol-4(5H)-ones were prepared containing a nitromethyl substituent in the side chain. Basing on the nitromethyl group of the latter nitrile oxide intermediates were generated that were brought into reaction of 1,3-dipolar addition with phenylacetylene, styrene, and vinyl ethyl ether with the formation of the corresponding isoxazole and isoxazoline derivatives.