Aleksandr M. Pinchuk

Electrophilic substitution as a convenient approach to functionalized N-benzyl-1,4-dihydropyridines

The reactivity of 1-benzyl-3-cyano-1,4-dihydropyridine was studied in reactions with electrophilic reagents based on structural analogy of 1,4-dihydropyridines with enamines. Different 5-functionalized derivatives were obtained by direct electrophilic substitution.

C-acylation of electron-rich heterocyclic compounds with Kirsanov isocyanate

Pyrroles, indoles, indolizines, and 2-methylfuran are vigorously C-acylated with isocyanatophosphoryl dichloride. The resulting heteroaryl-substituted isocyanatophosphoryl dichlorides provide a convenient access to a variety of products.© 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 343–348, 1999

Synthesis of Hexaisopropyltriamidephosphite: Myth or Reality?

Results of our work allowed us to assert that the methods for synthesis of triamide (i-Pr2N)3P 1 described are wrong.1–4 It was shown that diamidohalogenphosphites (i-Pr2N)2PHlg (Hlg = Cl,Br,I) do not react with di(isopropyl)amine even under harsh conditions such as heating up to 240◦C in various solvents. At the same time, less sterically hindered phosphenium cation 2 easily react with di(isopropyl)amine, affording diphosphine 5 instead of the expected triamide 1. The diphosphine 5 is also formed in the reaction of the phosphenium cation 2 with ketimine i-PrN = CMe2, with the reaction running via formation of monophosphine 3.

Synthesis and Properties of λ5-Phosphinines and λ5-Azaphosphinines

New accessible methods of synthesizing λ5-phosphines and 1,2-λ5-azaphosphinines by cyclocondensation of phosphorylated derivatives of linear enamines bearing at the α-position an electron-accepting substituent and a methyl group at the α-position was developed.