HO-Modification of Dialkyl [3-(Dialkylamino)-1-hydroxy-2,2-dimethylpropyl]phosphonates

Russian Journal of General Chemistry -     

Synthesis and properties of <Emphasis Type="Italic">O,O</Emphasis>-dialkyl [1-hydroxy-3-(dialkylamino)-2,2-dimethylpropyl]phosphonates

O,O-Dialkyl [1-hydroxy-3-(dialkylamino)-2,2-dimethylpropyl]phosphonates were prepared for the first time. By means of NMR ¹H, IR spectroscopy and quantum-chemical calculations the presence in them of various H-bonds was established. In the crystalline state P=O…HO intermolecular hydrogen bonds favor the formation of cyclic dimer associates D _P=O. In the liquid state and concentrated solutions P=O…HO and N…HO intermolecular hydrogen bonds cause the formation of cyclic dimer associates D _P=O and D_N, and intramolecular hydrogen bonds provide the existence of different conformations of the monomer form MN, the most stable among them with the non-strained six-membered …NCCCOH… ring.     

Synthesis of Dialkyl [1-Hydroxy-2,2-dimethyl-3-(dialkylamino)propyl]phosphonates

Russian Journal of General Chemistry -     

Synthesis of 9-[(2-hydroxy-1-phosphonylethoxy)ethyl]guanine, 1-[(2-hydroxy-1-phosphonylethoxy)ethyl]cytosine and 9-[(2-hydroxy-1-phosphonylethoxy)ethyl] adenine

The acyclic nucleoside phosphonate analogues, 9-[(2-hydroxy-1-phosphonylethoxy)ethyl]guanine 6 , 1-[(2-hydroxy-1-phosphonylethoxy)ethyl]cytosine 7 and 9-[(2-hydroxy-1-phosphonylethoxy)ethyl]adenine 8 , have been prepared by the coupling of a tosylate of the phosphonate side chain 12 with a purine or pyrimidine base followed by deprotection of the blocking groups.     

Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols

Structural alteration of the N^b-substituents of psilocin (3-[2-dimethylamino)ethyl]indol-4-ol) ( 12a ) has led to a number of compounds containing known pharmacophoric groups. Further, it is hoped that the subtle changes in the nature of these substituents may lead to a clearer understanding of the structure-activity relationships of the 4-hydroxytryptamine hallucinogens.     

Synthesis of 1-[2-(1H-Indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-ones

Russian Journal of General Chemistry - 1-[2-(1H-indol-3-yl)ethyl]-4-acetyl-3-hydroxy-5-phenyl-1H-pyrrole-2(5H)-ones were synthesized by the short heating of a mixture of tryptamine, aromatic...     

Rearrangement of 2,2′-dipropionylazoxybenzenes to 3-[1-alkoxy-1-(2-propionylarylamino)ethyl]benzo[c]isoxazoles

2,2-Dipropionylazoxybenzenes undergo rearrangement to the corresponding 3-[1-alkoxy-1-(2-propionylarylamino)ethyl]benzo[c]isoxazoles in the case of base catalysis; this transformation is realized only in the case of ortho,ortho' orientation of the propionyl groups in the substrate molecule and with the participation of the solvent as a reagent. A mechanism for the rearrangement that assumed the participation of one of the propionyl groups in intramolecular reduction of the azoxy group to an azo group is proposed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 743–748, June, 1983.     

Psilocin analogs. 1. Synthesis of 3-[2-(dialkylamino)ethyl] -and 3-[2-(cycloalkylamino)ethyl] indol-4-ols

The synthesis of four dialkyl and three eyeloalkyl analogs of psilocin (4, R - CH₃), a hallucinogenic principle found in certain fungi, is described. The synthetic route involves four transformations starting with 6,7-dihydroindol-4(5H)one: (1).     

Synthesis and Bioactivity of 5-Aryl-4-acyl-3-hydroxy-1-[2-(imidazolyl-3-yl)ethyl]3-pyrroline-2-ones

Russian Journal of General Chemistry - 5-Aryl-4-acyl-3-hydroxy-1-[2-(imidazolyl-3-yl)ethyl]-3-pyrroline-2-ones were synthesized by three-component reaction of methyl dioxobutanoates with aromatic...     

Synthesis of [2-(vinyloxy)ethyl]uracil and [2-(allyloxy)ethyl]uracil

A synthesis is reported for N¹-mono- and N¹,N³-disubstituted uracil derivatives containing a terminal carbon-carbon double bond in the side-chain. Alkylation of vinyl 2-chloroethyl ether by uracil potassium salts leads to a mixture of 1-[2-(vinyloxy)ethyl] and 1,3-di[2-(vinyloxy)ethyl] derivatives while treatment of 2,4-bis(trimethylsilyloxy)pyrimidines by vinyl 2-chloroethyl ether leads exclusively to N¹-monosubstituted products. Alkylation of cytosine by this chloroether gave 1-[2-(vinyloxy)ethyl]cytosine. The synthesis of 1-[2-(allyloxy)ethyl]uracil derivatives was carried out by treatment of uracil potassium salts by 1-(allyloxy)-2-(p-toluenesulfonyloxy)ethane.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 393–397, March, 1993.     

Synthesis of ethyl 3-(3-hydroxy-2-thienyl)-3-oxopropanoates

An approach to the synthesis of substituted ethyl 3-(3-hydroxy-2-thienyl)-3-oxopropanoates was developed based on the reaction of ethyl cyanoacetate, carbon disulfide, and ethyl 4-chloroacetoacetate. The reaction regioselectively involved the ester group, rather than the nitrile one like in the case when malononitrile or cyanacetamide were used.     

O,O-二乙基-N-[2-(3-乙酰基-2,2-二甲基-环丁基)-乙酰] 硫代磷酰胺合成及杀虫活性研究

α-蒎烯经过氧化、酰氯化制成蒎酮酰氯, 再与二乙基硫代膦酰胺反应, 合成了未见报道的标题化合物7, 经IR, MS, 1H NMR, 13C NMR等对标题化合物的结构进行了表征. 测试了标题化合物对甘蓝薄翅螟的毒力及其对敌百虫的增效作用. 初步生物活性测试结果表明, 标题化合物与敌百虫混合对甘蓝薄翅螟有明显的增效作用, 当标题化合物与敌百虫以3∶7的比例混合其增效作用最显著, 共毒系数(co-toxicity oefficient, CTC)为226.     

N'-芳基-N,N-二乙基乙二胺衍生物的合成及荧光性质研究

利用芳胺的N-烷基化反应,混酸硝化,硝基还原等原理合成了N'-2,6-二甲基苯基-N,N-二乙基乙二胺及其衍生物,利用IR光谱和1HNMR测试技术对化合物进行了表征.对所合成的化合物和原料进行了吸收和荧光光谱的测定及分析,探讨了化合物的结构与光谱之间的关系.探索了在酸碱等条件下荧光光谱的变化规律.