Insect pheromones and their analogues XXV. Synthesis of acetylenic precursors of pheromones from undecylenic acid

The selective ozonolysis of pentadec-1-en-12-yne and heptadec-1-en-12-yne, synthesized from the readily available undecylenic acid, has given tetradec- and hexadec-11-yn-1-ols — acetylenic precursors of a number of pheromones of insects of the order Lepidoptera. Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 823–825, November–December, 1990.     

Positive- and negative-ion mass spectra of racemic diptocarpamine and its sulfide precursor

Features of the fragmentation on electron impact and resonance electron capture of racemic diptocarpamine (I), its sulfide precursor (II), and N-decyl-N-isopropylurea have been determined which consist in a predominance of simple bond cleavages over the rearrangement processes involving the elimination of S(O)NH-containing neutral fragments that are typical for diptocarpidine. The elementary compositions of the characteristic lines in the EI mass spectra were established by measuring accurate values of the mass numbers of the ions. An estimate of the efficacy of the spatial interaction of the heteroatomic groupings separated by carbon chains in the and M^– ions of compounds (I) and (II) has been made. On the basis of the REC mass spectra it has been concluded that the molecules of compounds (I) and (II) exist in twisted or folded conformations.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 80–86, January–February, 1989.     

Specificity of the reaction of 2,3-dichloro-4,4-dimethoxy-5-(2-methylfuran-3-yl)cyclopent-2-en-1-one with amines

2,3-Dichloro-4,4-dimethoxy-5-(2-methylfuran-3-yl)cyclopent-2-en-1-one reacted with diethyl-and dipropylamines to give products of Ad_NE replacement of the chlorine atom at the vinylic C³ atom and substitutive opening of the furan ring with simultaneous deprotection of the dimethyl acetal moiety in the 2,3-dichlorocyclopentenone fragment.     

Negative-ion mass spectra of the synthetic alkaloid diptocarpilidine and its deoxy precursor

The existence of the molecules of the synthetic alkaloid diptocarpilidine in a folded conformation as a consequence of the intramolecular interaction of the sulfoxide and cyano groups through space has been established by negative-ion mass spectrometry. Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 543–546, September–October, 1992.     

Synthesis of N-(o- and p-Alkenylphenyl)-Substituted Quinazolin-4-ones

Alkenylphenyl-substituted quinazolinones were prepared by reactions of 2-methyl-4H-3,1-benzoxazin-4-one with o- and p-alkenylanilines.     

Some aspects of selective ozonolysis of 5-allyl(allenyl)-4,4-dimethoxy-2,3,5-trichlorocyclopent-2-enones and their 3-morpholino derivatives

Ozonolysis of the title cyclopentenones proceeds selectively with the participation of exocyclic multiple bonds. In the case of 5-allyl derivatives, the corresponding ozonides were isolated along with the expected products. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 343–346, February, 1999.     

Cross-combination of magnesium diacetylenides with organic halides catalyzed by transition metals complexes

Conclusions The cross-combination of magnesium diacetylenides of the type (R-CC)₂Mg (R=C₅H₁₁, Ph) with alkyl-, allyl-, propargyl-, and arylhalides, catalyzed by Cu(I), Ni, and Pd complexes, gives mono- and disubstituted acetylenes with high yields.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2037–2041, September, 1987.