Unusual reaction of α-diketones of the indole series with hydrazine

Symmetrical and unsymmetrical α-diketones of the indole series were synthesized by the Friedel-Crafts reaction of 3-indolylglyoxyl chlorides with heterocycles. A nonconventional reaction of N-unsubstituted diketones with hydrazine producing 3H-pyrazolo[3,4-c]quinoline derivatives was found. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 862–866, May, 2006.     

Synthesis of 4-hetaryl-5,6-(2,5-dimethyl-3-thienyl)-2-phenyl-4h-thiazines and investigation of their photochromism

The polar [4+2] cycloaddition reaction of 1,2-bis(2,5-dimethyl-3-thienyl)acetylene with thiobenzamide and certain aldehydes of the thiophene and furan series catalyzed by boron trifluoride etherate gives the corresponding 4-hetaryl-5,6-di(2,5-dimethyl-3-thienyl)-2-phenyl-4H-1,3-thiazines. The photochromic properties of the products have been studied.__________Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 100–106, January, 2005.     

Nonmetallic Wurtz coupling reaction of perfluorohexyl iodide

It is shown for the first time that the Wurtz reaction can be realized by the action of an organic substance (triphenylphosphine) on an alkyl halide (perfluoroalkyl iodide) without the use of metals. It was found that when trying to prepare the bis(3,3′-aminophenyl)(fluoroalkyl)phosphine oxide by four-step synthesis, in the first stage of the reaction of perfluoro-1-iodohexane with triphenylphosphine does not proceed towards the formation of an intermediate quaternary phosphonium salt. Instead, the carbon chain of perfluoroalkyl iodide dimerizes to form perfluorododecane – Wurtz reaction product. We have proposed a new pathway for homocoupling of perfluoroalkylhalides into even-numbered perfluoroalkanes.     

Synthesis and cytotoxic activity of Boc-protected pentapeptide amide analogs of somatostatin

Russian Chemical Bulletin - New Boc-protected pentapeptide amides of the general formula Boc—Cys(Boc)—Phe—d-Trp—Lys(Boc)—Thr—NHR, which are analogs of the...     

Synthesis of bis-and tetrakis-(ω-dimethylamino)-substituted cross-conjugated polyene α-diketones of the thiophene series

Bis-and tetrakis(ω-dimethylamino)-substituted cross-conjugated polyene α-diketones, containing two thiophene rings, were synthesized from α-diketones of the thiophene series and β-dimethylaminoacrolein aminals and also 2-aza-3-dimethylaminoacrolein acetal. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 841–847, June, 2006.     

Synthesis of new quinazoline-containing hydroxamic acids as potential HDAC/VEGFR inhibitors. Unusual rearrangements with pyrrolidone ring opening and dehydration of 3-N-hydroxyquinazoline fragment containing tetracycles

Synthesis pathways were developed and new hydroxamic acids were obtained as potential inhibitors of HDAC/VEGFR2, including tetracycles containing quinazolinone fragment as a “cap”. Further biological testing of the obtained compounds will give an opportunity to estimate the real prospects of the chosen research direction.     

A New Approach to the Synthesis of Dithienylethanediones and Dithienylacetylenes

1,2-Dithienylethanediones were synthesized by modified acylation of thiophene and its homologs in the presence of aluminum chloride and pyridine. The bishydrazones of the products were converted into dithienylacetylenes by oxidation with atmospheric oxygen in pyridine in the presence of CuCl.     

Synthesis and properties of 1,2-dihydro-4(3<Emphasis Type="Italic">H</Emphasis>)-quinazolinones

We modified the preparative-scale method for the synthesis of 2-aryl 1,2-dihydro-4(3H)-quinazolinone derivatives obtained in high yields by the reaction of new and commercially available aromatic aldehydes with anthranilic acid amides. A series of quinazolinone derivatives possessing anticancer and antiparasitic activities, as well as capable of preventing the progress of neurodegenerative diseases were characterized. There are grounds for clinical trials of these substances in order to select compounds being promising for clinical application.