Synthesis of 1,4-dihydro-2-methyl-4-oxo-3-quinolineglyoxylic acid and related compounds

The synthesis of 1,4-dihydro-1-methoxy or ethyl -2-methyl-4-oxo-3-quinolineglyoxylic acid derivatives are described. α-Acetoxy-1,4-dihydro-1-hydroxy-2-methyl-4-oxo-3-quinolineacetic acid esters ( 7a, 7a ), which are key intermediates, were prepared by catalytic hydrogenation of 2-acetoxy-3-acetyl-4-hydroxy-4-(2-nitrophenyl) crotonic acid lactone ( 6 ) in methanol or ethanol.     

Synthesis of bulgecinine: a new amino acid in bulgecins

Bulgecinine, a new proline type amino acid in bulgecins, was synthesized stereospecifically by use of D-glucose as a chiral precursor.     

Regioselectivity in the addition of alkanethiols to vinylacetylene in superbasic media of alkali-metal hydroxides in dimethyl sulfoxide

Conclusions The reaction of vinylacetylene with alkanethiols is largely directed toward the formation of alkyl 1,3-butadien-l-yl sulfide with increasing basicity of the system consisting of an alkali-metal hydroxide and DMSO. A reduction in the basicity facilitates the formation of alkyl 2,3-butadien-l-yl sulfide.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2800–2803, December, 1985.     

Condensation of α-ethoxyacrolein with secondary amines

Conclusions Morpholine, piperidine, and dibutylamine undergo both 1,2 and 1,4 addition to -ethoxyacrolein to form a mixture of 3,3- and 1,3-diamino-2-ethoxy-1-propenes. The N-formyl derivative of the starting amine is a side product. The reaction of -ethoxyacrolein with diethylamine gives only splitting of the C-C bond and formation of N-formyldiethylamine.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2610–2612, November, 1985.     

Reaction of α-alkoxyacroleins with acetone cyanohydrin

Conclusions -Alkoxyacroleins add acetone cyanohydrin in the presence of piperidine to give 1-N-piperidino-1-cyano-2-alkoxy-2-propenes, which in the presence of piperidine or on long storage are isomerized to 1-N-piperidino-1-cyano-2-alkoxy-1-propenes.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2122–2124, September, 1973.