2-(5-Bromo-2-furyl)quinoxaline and 3-(5-bromo-2-furyl)-2-quinoxalone

2-(5-Bromo-2-furyl)quinoxaline and 3-(5-bromo-2-furyl)-2-quinoxalone were obtained by the action of bromine on the corresponding quinoxaline derivatives and also by condensation of o-phenylenediamine with, respectively, (5-bromo-2-furyl)glyoxal or (5-bromo-2-furyl)glyoxylic acid esters.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 404–406, March, 1973.     

Synthesis and properties of 2-(2-furyl)-and 2-(2-Thienyl)-1,3-benzoxazoles

Condensation of o-aminophenol with furoyl and thenoyl chlorides in 1-methylpyrrolidin-2-one gave, respectively, 2-(2-furyl)- and 2-(2-thienyl)-1,3-benzoxazoles in which the furan and thiophene rings showed no acidophobic properties. Reactions of 2-(2-furyl)- and 2-(2-thienyl)-1,3-benzoxazoles with electrophilic reagents (acylation, bromination, nitration, and sulfonation) afforded products of hydrogen replacement in both hetaryl and benzene rings, depending on the conditions.     

Synthesis and properties of 1-methyl-2-phenyl-5-(2-furyl)- and 1-methyl-2-phenyl-5-(2-thienyl)imidazoles

2-Phenyl-5-(2-furyl)- and 2-phenyl-5-(2-thienyl)imidazoles were synthesized by condensation of 2-furoylmethyl and 2-thenoylmethyl acetates with benzaldehyde under the conditions of Weidenhagen reaction. The products were converted to N-methyl derivatives in the KOH-acetone system. The electrophilic substitution reactions of the products (acylation, bromination, nitration, sulfonation, hydroxymethylation) were studied.     

Synthesis of 2-phenyl-3-(2-furyl) — and 2-phenyl-3-[β-(2-furyl)vinyl]-1,2-dihydro-naphtho[1,2-d]-1,2,4-triazines

The corresponding 2-phenyl-3-(2-furyl)- and 2-phenyl-3-[-(2-furyl)vinyl]-1,2-dihydronaphtho-[1,2-d]-1,2,4-triazines were obtained by heating Schiff bases [prepared by reaction of 1-(phenyl-azo)-2-aminonaphthalene with furfural, -(2-furyl)acrolein, and their 5-bromo and 5-nitro derivatives] in glacial acetic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 158–160, February, 1973.     

Photoreaktionen des 3-(2-Thienyl)-2,2-dimethyl-2H-azirins

Synthesis and Photochemistry of 3-(2-Thienyl)-2,2-dimethyl-2H-azirine The synthesis of 3-(2-thienyl)-2,2-dimethyl-2 H-azirine (1) is described. UV. irradiation of 1 in benzene solution generates the nitrile isopropylide 2 which reacts in a regiospecific manner with activated C, C and C, O double bonds to give 1-pyrrolines and 3-oxazolines, respectively. With chelidonic acid diethyl ester the cycloaddition of 2 to the C, C double bond is preferred.     

Solid-state structures of cis- and trans-1-cyclohexyl-2-phenyl-3-(p-toluyl)aziridines

Solid-state structures have been determined for cis- and trans-1-cyclohexyl-2-phenyl-3-(p-toluyl)aziridines using single-crystal X-ray diffraction techniques. The cis isomer crystallizes in the centrosymmetric monoclinic space group P2₁/c (No. 14), with a = 18.669(3)Å, b = 5.709(1)Å, c = 17.412(2)Å, β = 96.29(1)° and Z = 4; the trans isomer crystallizes in the noncentrosymmetric orthorhombic space group Pna2₁ (No. 33), with a = 17.089(2)Å, b = 18.729(3)Å, c = 5.749(1)Å and Z = 4. Full-matrix least-squares refinement of the structural parameters led to the following final agreement factors: R₁ (unweighted, based on F) = 0.040 and R₂ (weighted, based on F) = 0.054 for the 2592 independent reflections of the cis isomer having 2θ_MoK¯α <55° and I>3σ₁, and R₁ = 0.033 and R₂ = 0.031 for the 1504 independent reflections of the trans isomer having 2θ_MoK¯α <55° and I>3σ₁. The statistically significant differences that exist between the two isomers for two bond lengths and ten bond angles (p < 0.05) appear to be the direct result of the p-toluyl group orientation with respect to the cyclohexyl and phenyl substituents. In the cis isomer it is anti with respect to the N-cyclohexyl group and cis with respect to the phenyl group, whereas in the trans isomer it is syn with respect to the N-cyclohexyl and trans with respect to the phenyl group. Three-ring to carbonyl hyperconjugation is correlated with stereoelectronic interactions in the trans isomer. Bonding, determined by X-ray and nmr studies, is discussed for the three-membered aziridine ring proper; while bonding, determined by X-ray studies, is discussed for substituents of the aziridine ring. These aziridinyl ketone compounds are of importance as potential mammalian DNA alkylating anti-tumor agents in solid-state solid-state systems. To date only a trans isomer has demonstrated this biological activity in tumor-bearing rats.