Cyclic derivatives of 3-fluoro-3,3-dinitro-1-aminopropane

Conclusions A study was made of the preparation and nitrolysis of some cylic derivatives of 3-fluoro-3, 3-dinitro1-aminopropane, and the differences in the reactivity of the latter compound and the behavior of 3,3,3-trinitro-1-aminopropane in the same reactions were pointed out.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1369–1371, June, 1973.     

Aminotriazoles in the mannich reaction

Summary 4-(2,2-Dinitropropyl)amino-1,2,4-triazoles are the products obtained by the condensation of 4-amino-l,2,4-triazole and its hornologs with formaldehyde and gem-dinitroethane. Condensation products containing two molecules of the amine were not found.     

Carboxyimidazoles in the mannich reaction

Depending on the reagent ratio, 5-dimethylaminomethyl-4-imidazole-4-carboxylic acid and 2,4,5-tris(dimethylaminomethyl)imidazole were obtained in the aminomethylation of imidazole-4-carboxylic and imidazole-4,5-dicarboxylic acids. The oxidation of these compounds with nitric acid leads to imidazole-4,5-dicarboxylic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 206–208, February, 1989.     

Organocatalytic stereoselective mannich reaction of 3-substituted oxindoles

The asymmetric Mannich reaction of 3-substituted oxindoles and N-Boc imines was investigated for the first time, employing bifunctional thiourea-tertiary amine organocatalysts based on DPEN scaffold. The novel transformations exhibited high diastereoselectivities, and the Mannich adducts bearing adjacent quaternary and tertiary chiral centers were generally obtained in good to excellent enantioselectivities (up to 95% ee).     

3,3-二硝基氮杂环丁烷和1,1''''-亚甲基-双(3,3-二硝基-1-氮杂环丁烷)的合成研究

3,3-二硝基氮杂环丁烷(DNAZ)的含能盐及衍生物是一类重要的高能量密度材料,因此DNAZ的合成和应用受到了密切关注.采用新的合成方法,以1-叔丁基-3,3-二硝基氮杂环丁烷为起始原料,以76.3%的总收率得到了DNAZ,然后以DNAZ为原料,与多聚甲醛反应,得到了1,1'-亚甲基-双(3,3-二硝基-1-氮杂环丁烷)(DNAZ-CH2-DNAZ).用红外和核磁共振光谱等对各化合物的结构进行了表征.     

Secondary-tertiary acetylenic δ-glycols in the mannich reaction

Conclusions Some acetylenic bis(diethylaminomethyl) ethers were obtained by the reaction of secondary-tertiary acetylenic -glycols with diethylamine by the Mannich reaction.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2824–2825, December, 1970.     

Linear aminophenol polymers using the mannich reaction

Mannich reactions were used to prepare a series of low-molecular-weight linear polymers from substituted phenols, formaldehyde, and secondary diamines. The physical and spectroscopic properties of these new aminophenol polymers are described and compared with those of the bisphenolic diamines formed as an intermediate step in the polymerization process. The polymers were found to give coloured, water-soluble, metal complexes with copper and iron salts.     

The use of amino acids in the mannich reaction

Amino acids have been found to participate as the amine component in the Mannich reaction with both ketones and phenols. The phenolic Mannich bases may be cyclized with sulfuric acid to 1,2-dihydro-4(3/H)isoquinolones. In the presence of thionyl chloride the same Mannich bases undergo lactonization to benz[f]-1,4-oxazepin-4(3H)ones.     

The investigation of the mannich reaction of 4,5-dimethyl-1,2-dithiole-3-thione

4,5-Dimethyl-1,2-dithiole-3-thione 1 reacts with primary amines and formaldehyde to give the mono-, retro-, bis-Mannich bases in moderate yield.     

Use of the mannich reaction in the synthesis of bispidine

A three-step synthesis of bispidine ( 1 ) is described. Mannich condensation of N-benzyl-4-piperidone, formaldehyde, and benzylamine afforded N,N′-dibenzylbispidinone ( 5 ), which was reduced under modified Wolff-Kishner conditions to yield N,N′ -dibenzylbispidine ( 6 ). Catalytic debenzylation of this compound gave 1 .     

Synthesis of N-propargylanabasine derivatives by the mannich reaction

N-Propargylanabasine derivatives bearing various substituents at the carbon atom of the alkyne fragment were obtained by the reaction of anabasine hydrochloride with terminal alkynes and paraformaldehyde. The reaction proceeded with retention of the C(2) chiral center in anabasine fragment. The by-products of the reaction, including 1,3-diacetylene (the products of dimerization of alkynes) and conjugated vinylacetylenes (the rearrangement products of the Mannich adducts) were isolated and characterized. Dedicated to Academician V. A. Tartakovsky in honor of his 75th anniversary. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1576–1585, August, 2007.     

Synthesis of 3, 5-dinitro-1-cyclopentene

Conclusions Cyclopentadiene easily adds nitrogen tetraoxide with the formation of 3, 5-dinitro-1-cyclopentene.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2108–2111, September, 1970.     

Isothiazoles VII: N-hydroxyalkylation and mannich reaction of 4-isothiazolin-3-one

Hydroxyalkylation and the synthesis of Mannich bases of 4-isothiazolin-3-one are described. Conversion of hydroxyalkyl to haloalkyl derivatives and the preparation of 2-arylcarbamoyloxy-methyl-4-isothiazolin-3-ones are also reported.