Novel Chiral Building Block: (2R,3S)-2-(1,3-Dithian-2-yl)-3-hydroxybutanoates. Highly Diastereo- and Enantioselective Baker's Yeast Reduction of 2-(1,3-Dithian-2-yl)-3-oxobutanoates

The baker's yeast reduction of 2-(1,3-dithian-2-yl)-3-oxobutanoates gave (2R,3S)-2-(1,3-dithian-2-yl)-3-hydroxybutanoates in good yiels and in high diastereo- and enantioselectivity.     

Synthesis of 2-(pyrimidin-4-yl)indoles

The synthesis of 2-substituted isomers of the meridianins, a familiy of bioactive indole alkaloids isolated from the tunicate Aplidium meridianum, was undertaken. The synthetic route comprises six steps, with a microwave promoted Fischer cyclization as the key reaction.     

Synthesis of 2-alkyl-3-(2-benzoxazolon-3-yl)indoles

It was shown that 3-(2-oxoalkyl)-2-benzoxazolones with phenylhydrazine in the presence of polyphosphoric acid form the corresponding 2-alkyl-3-(2-benzoxazolon-3-yl)-indoles.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1086–1087, August, 1984.     

Synthesis of New 2-(Oxiran-2-yl)-1,3-oxazoles

Russian Journal of General Chemistry - Reaction of 2-chloro-N-(2,2-dichloro-1-cyanovinyl)acetamide with dimethylamine gave 5-(dimethylamino)-2-[(dimethylamino)methyl]-1,3-oxazole-4-carbonitrile,...     

Synthesis of 2-(dibenzosuberen-5-yl)-1,3-dicarbonyl compounds

Reaction of dibenzosuberen-5-ol with 1,3-dicarbonyl compounds catalyzed with scandium(III), copper(II), or indium(III) triflate (5 mol %) afforded 2-(dibenzosuberen-5-yl)-1,3-dicarbonyl compounds in 63–86% yield.     

Synthesis of 1,3-dialkyl-5-(hetaryl-1-yl)-1,3-dihydrobenzimidazol-2-ones

Reactions of 5-amino-1,3-dialkyl-1,3-dihydrobenzimidazol-2-ones with 2,5-dimethoxytetrahydrofuran and 2,6-dimethyl-γ-pyranone led to the formation of 1,3-dialkyl-1,3-dihydro-5-(pyrrol-1-andл)benzimidazol-2-ones and 1-(1,3-dialkyl-2-oxo-1,3-dihydrobenzimidazol-5-yl)-2,6-dimethylpyridin-4-ones.     

Synthesis and reactivity of 2-(porphyrin-2-yl)-1,3-dicarbonyl compounds

A simple and efficient procedure for the synthesis of porphyrins bearing 1,3-dicarbonyl moieties at the β-position is described. The new compounds were further functionalized and new derivatives containing an heterocyclic ring, an ethyl acetate residue or a 2-oxopropyl group at the β-position have been obtained.     

Synthesis and isomerization reaction of 2-(benzoxazol-2-yl)-1,3-tropolones

An acid-catalyzed reaction of 2-methylbenzoxazole with 3,4,5,6-tetrachloro-1,2-benzoquinone leads to 2-(benzoxazol-2-yl)-5,6,7-trichloro-1,3-tropolone and 2-(benzoxazol-2-yl)-4,5,6,7-tetrachloro-1,3-tropolone. 1,3-Tropolones upon reflux in ethyl alcohol undergo the rearrangement resulted in the seven-membered ring contraction to form ethyl 2-(benzoxazol-2-yl)-5,6-dichloro-3-hydroxybenzoate and ethyl 2-(benzoxazol-2-yl)-4,5,6-trichloro-3-hydroxybenzoate. The molecular structure of the latter was established by X-ray diffraction analysis.     

Synthesis and molecular structure of 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazines

Reactions of some 2-hydrazinopyrimidine hydrochlorides with potassium thiocyanate gave 1-(pyrimidin-2-yl)thiosemicarbazides which underwent Hantzsch condensation with aryl chloromethyl ketones to produce 1-(pyrimidin-2-yl)-2-(4-aryl-1,3-thiazol-2-yl)hydrazine hydrochlorides. The protonation was accompanied by mutually dependent tautomeric rearrangements of heterocyclic fragments.     

Synthesis of 2-(1,3-Diselenan-2-yl)thiophene from 1,3-Propanediselenol and 2-Thiophenecarbaldehyde

Russian Journal of Organic Chemistry -     

1,3-丙二硫醇替代试剂1-（1,3-二噻-2-亚基）丙酮的缩硫醛/酮化反应

通过易制备的3-(1,3-二噻-2-亚基)-2,4-戊二酮(1b)在酸性条件下的脱乙酰化反应制得1-(1,3-二噻-2-亚基)丙酮(1f),产率为86%. 在MeCOCl/MeOH体系中,常温或回流条件下,化合物1f能作为有效的1,3-丙二硫醇替代试剂与醛和酮进行缩硫醛/酮化反应,高产率(86%～99%)合成1,3-二噻烷衍生物. 与已报道的替代试剂2-(2,4-二氯-1,4-戊二烯-3-亚基)-1,3-二噻烷(1a)、3-(1,3-二噻-2-亚基)-2,4-戊二酮(1b)、2-(1,3-二噻-2-亚基)-3-羰基丁酸甲酯(1c)、2-(1,3-二噻-2-亚基)-3-羰基丁酰胺(1d)和2-(1,3-二噻-2-亚基)-3-羰基丁酸(1e)相比,化合物1f是活性最好的1,3-丙二硫醇替代试剂.     

Synthesis of Geminally Activated 4-(Furan-2-yl)- and 4-(Thiophen-2-yl)-1-nitrobuta-1,3-dienes

The condensation of 3-(furan-2-yl)- and 3-(thiophen-2-yl)prop-2-enals with nitro-substituted CH acids, namely ethyl nitroacetate, nitroacetone, nitroacetophenone, and nitroacetonitrile, afforded a series of geminally activated nitro dienes, 4-(furan-2-yl)- and 4-(thiophen-2-yl)-1-nitrobuta-1,3-dienes. The product structure was confirmed by NMR and IR spectroscopy.

     

Synthesis of 2-(alkylthio)indoles

Treatment of 3-(alkylthio)indoles 3 with trifluoroacetic acid, neat (for 3a,b) or in dichloromethane solution (for 3c,d) at room temperature gave the corresponding 2-(alkylthio)-indoles in high yields (85–90%). The interconversion is complete and does not involve an acid-induced equilibrium between the two isomers; a mechanistic rationale is provided.     

2-(1,3-亚丙二硫)亚甲基-3-羰基丁酸作为硫醇替代试剂在缩硫醛/酮化反应中的应用

探讨了以2-(1,3-亚丙二硫)亚甲基-3-羰基丁酸作为硫醇替代试剂,乙醇作溶剂的缩硫醛/酮化反应.实验结果表明,该硫醇替代试剂能与各类醛、酮化合物快速、顺利地进行缩硫醛/酮化反应,以较高的产率生成相应的1,3-二噻烷类化合物.同时,该缩硫醛/酮化反应对不同的醛、酮化合物具有较高的化学选择性.     

Synthesis and structure of 4,6-di(tert-butyl)-2-(4-chloro-7,8-dimethylquinolin-2-yl)-7-(piperidin-1-ylmethyl)-1,3-tropolone

Russian Chemical Bulletin - The reaction of 4-chloro-2,7,8-trimethylquinoline with 4,6-di(tert-butyl)-3-(piperidin- 1-ylmethyl)-1,2-benzoquinone, which was prepared by the in situ oxidation of...     

Synthesis and transformations of polyhedral compounds. Synthesis of 2-[quinolin-3(2)-yl]-1,3-diazaadamantanes

A number of new 1,3-diazaadamantane derivatives containing quinoline fragments on C² have been synthesized by condensation of 1,5-dialkyl-3,7-diazabicyclo[3.3.1]nonan-9-one, 1,5-dimethyl-3,7-diazabicyclo-[3.3.1]nonan-9-ol, and 1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonane with 2-oxo-1,2-dihydroquinoline-3-carbaldehyde, 2-chloro- and 2-iodoquinoline-3-carbaldehyde, and quinoline-2-carbaldehyde.     

Synthesis of new physiologically active (2-oxoimidazolidin-5-yl)indoles

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