Unusual insertion of product the reaction of 3,3-dichloropenlanedione with aromatic aldehydes

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, p. 183, January, 1994.     

Novel synthesis of 4-halo-3-hydroxy-2-pyrone: one pot rearrangement-cyclization reaction by magnesium halide

Treatment of acetonide protected 4,5-dihydroxy-2-chloroglycidic ester or its rearrangement product, the acetonide protected 4,5-dihydroxy-3-chloro-2-oxo ester, with magnesium halides gave 4-halo-3-hydroxy-2-pyrone in excellent to reasonable yields in one pot. The mechanism of this novel one pot rearrangement-cyclization reaction is also proposed.     

Molecular and crystal structures of 5,7-dichloro-4-nitro-2,1,3-benzoxadiazole and products of its reactions with secondary amines

The molecular and crystal structures of 5,7-dichloro-4-nitro-2,1,3-benzoxadiazole and products of its reactions with hexamethyleneimine and dimethylamine were established by X-ray diffraction analysis. The molecular structures and the systems of hydrogen bonds in the crystals of these compounds are discussed.     

Synthesis and study of the light-stabilizing activity of some dithiocarbamates that include a heteroaromatic ring

A number of new dithiocarbamates of transition metals that contain thiophene, furan, benzo[b]thiophene, and benzo[b]selenophene rings were synthesized. The compounds obtained were investigated as light stabilizers for polymers. It is shown that the effectiveness of the light-stabilizing effect of the dithiocarbamate depends on the structure of the heterocyclic fragment included in its composition.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1482–1488, November, 1982.     

Condensed heterocycles. 44. Synthesis and structure of imines of 2-mercaptobenzo[b]-furan-3-carbaldehydes and 3-mercaptobenzo[b]furan-2-carbaldehydes and their derivatives

A number of isomeric mercapto aldimines of benzo[b]furan have been obtained and their structure and properties have been studied in comparison with their benzo[b]-thiophene analogs. It has been shown that the nature of the heterocycle has no substantial influence on the structure and properties of these compounds, in contrast to the initial mercapto and hydroseleno aldehydes. It has been observed that the 2-mercapto or 2-methylthio(methylseleno) groups in benzo[b]furan-3-carbaldehydes are readily replaced by an amino group, while they are not replaced in the isomeric 3-mercapto- and 3-methylthio(methylseleno)benzo[b]furan-2-cabaldehydes.For communication 43, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 598–602, May, 1985.     

7,7-Dimethyl-2,10-epoxybicyclo[3.1.1]heptane. Synthesis,Structure, and Products of Epoxide Ring Cleavage

7,7-Dimethyl-2,10-epoxybicyclo[3.1.1]heptane obtained by treatment of (-)--pinene with peroxybenzimidic acid has configuration.     

Halo Derivatives of 2,4-Dinitrothiolene 1,1-Dioxides: Synthesis and Structure

Procedures were developed for preparing representatives of a new type of halonitrothiolene 1,1-dioxides: mono- and dihalo derivatives of 2,2,4-tri- and 2,4-dinitro-3-thiolene 1,1-dioxides. An X-ray diffraction study showed that 2,5-dinitro-2,3-dichloro-3-thiolene 1,1-dioxide molecules exist in the crystal as enantiomeric pairs; the five-membered rings have the envelope conformation, with deviation of the sulfur atom from the ring plane; the halogen atom and nitro group at the multiple bond are essentially coplanar with the ring.     

Synthesis and properties of N-methylmorpholinium 4aryl-6-methyl-5-phenylcarbamoyl-3cyano-1,4dihydropyridine-2-thiolates. Molecular and crystalline structure of 2allylthio-6-methyl-5-phenylcarbamoyl-4-(2chlorophenyl)-3-cyano-1,4-dihydropyridine

By the condensation of an aromatic aldehyde, the anilide of acetoacetic acid, cyanothioacetamide, and Nmethylmorpholine, substituted N-methylmorpholinium 1,4-dihydropyridine-2-thiolates have been synthesized and subsequently used in the synthesis of the corresponding thiones, 2-alkylthiopyridines, thieno[2, 3b]pyridines, and disulfides. X-ray diffraction has been used to establish the structure of 2-allylthio-6-methyl-5phenylcarbamoyl-4-(2-chlorophenyl)-3-cyano-1, 4-dihydropyridine.T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Russian Academy of Sciences, Moscow 117813. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1243–1251, September, 1996. Original article submitted May 13, 1996.     

Mannich reaction in the synthesis of N,S-containing heterocycles. 1. Synthesis of novel derivatives of imidazo[2,1-<Emphasis Type="Italic">b</Emphasis>][1,3,5]thiadiazine

Reactions of (Z)-5-benzylidene-2-thiohydantoin with formaldehyde and primary aromatic amines afforded novel derivatives of imidazo[2,1-b][1,3,5]thiadiazine in 50–69% yields. Dedicated to Academician N. S. Zefirov on the occasion of his 70th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2158–2160, September, 2005.     

Crystal and molecular structure of 2-phenyl-2-thiono-5,6-(4′,5′-dimethylbenzo)-1,3,2-dithiaphosphepine and 2-methoxy-2-oxo-5,6-benzo-1,3,2-dioxaphosphepine

A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Branch, Academy of Sciences of the USSR. Translated from Zhurnal Strukturnoi Khimii, Vol. 31, No. 5, pp. 75–80, September–October, 1990.