Synthesis ofN-(imidomethyl)glycine esters from alkyl glycinates,imides of dicarboxylic acids,and formaldehyde

A method for preparingN-(imidomethyl)glycine esters by the reaction of alkyl glycinates with formaldehyde and imides has been developed.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1306–1307, July, 1995.     

Chemical properties ofN-(amidomethy)- andN-(imidomethyl)glycine derivatives 2. Reactions at alkoxycarbonyl and carboxyl groups

N-(Aroylarnmomethylfglycine amides were synthesized by reactions ofN-(aroyllminomethyl) glycine esters with ammonia. Alkaline hydrolysis ofN-(amidomethyl)glycine,N-(irnidornethyl)glycine, andN-(amidomethyl)pheriylalariiiie esters afforded the correspondingN-(amidowthyVa-amirio acids- Reactions of the Last-mentioned compounds with ethyl esters of glycine, alanine, and phenylalanine in the presence of dicyclohexylcarbodiimide yielded dipeptides containingNh-amidomethyl substituents.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1770–1771, July, 1996.     

Synthesis ofN-(3-azido-2-nitroxypropyl)-,N-(2,3-diazidopropyl)-, andN-(2-azido-3-methoxypropyl)-N-alkylnitramines

N-(3-Azido-2-nitroxypropyl)-N-alkylnitramines andN-(2,3-diazidopropyl)-N-alkylnitramines were prepared by nitration and azidation ofN-alkyl-N-(2-hydroxy-3-chloropropyl)sulfamates andN-(3-azido-2-hydroxypropyl)-N-alkylsulfamates. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 206–208, January, 1999.     

Thermal,spectral and magnetic studies on glycine complexes of cobalt(II), nickel(II) and zinc(II) with hydrazine

Hydrazinium metal glycinates [(N₂H_{5 2}M(NH₂CH₂COO)₄] and bis(hydrazine)metal glycinates, [M(NH₂CH₂COO)₂(N₂H₄)₂], whereM=Co, Ni or Zn have been prepared and characterized by chemical analyses, magnetic moments and vibrational and electronic spectra. The thermal behaviour of these compounds has been studied by thermogravimetry and differential thermal analyses. These complexes decompose with high exothermicity giving metal powder as the final residue. The X-ray powder data of each set of complexes show isomorphism among themselves.     

芳香胺参加的Mannich反应——3-芳氨基-3-苯基-1-(4-溴苯基)丙酮的合成

文献报道过芳香胺与苯甲醛生成的Schiff碱可在少量相应的芳香胺盐酸盐或浓盐酸催化下制备Mannich碱(Ⅰ),所用的Schiff碱系事先合成,且产率较低(15-68.9％)。本文报导用4-溴苯乙酮、苯甲醛和芳香胺在少量浓盐酸催化下能直接发生Mannich反应,     

Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)-benzoxazolones

In this study, a new series of Mannich bases, 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2( 3H )-benzoxazolones ( 1a–g ), were synthesized by the Mannich reaction. Inhibitory effects of the newly synthesized compounds towards carbonic anhydrases (CAs) and acetylcholinesterase (AChE) enzymes were evaluated to find out new potential drug candidate compounds. According to the inhibitory activity results, K_i values of the compounds 1 and 1a–g were in the range of 12.3 ± 1.2 to 154.0 ± 9.3 nM against hCA I, and they were in the range of 8.6 ± 1.9 to 41.0 ± 5.5 nM against hCA II. Ki values of acetazolamide (AZA) that was used as a reference compound were 84.4 ± 8.4 nM towards hCA I and 59.2 ± 4.8 nM towards hCA II. K_i values of the compounds 1 and 1a–g were in the range of 35.2 ± 2.0 to 158.9 ± 33.5 nM towards AChE. K_i value of Tacrine (TAC), the reference compound, was 68.6 ± 3.8 nM towards AChE. Furthermore, docking studies were done with the most potent compounds 1d , 1g , and 1f (in terms of hCA I, hCA II, and AChE inhibition effects, respectively) to determine the binding profiles of the series with these enzymes. Additionally, the prediction of ADME profiles of the compounds pointed out that the newly synthesized compounds had desirable physicochemical properties as lead compounds for further studies.     

Synthesis of 2([Methyl-5-[(E)-2-aryl-1-ethenyl]-4-isoxazolyl]imino)-1,3-thiazolan-4-ones and Their Mannich Bases

Isoxazolyl chloroacetamides (2) were obtained from 4-amino-3-methyl-5-styrylisoxazoles (1) on reaction with chloroacetyl chloride. Cyclocondensation of 2 with NH₄SCN yielded 2([-methyl-5-(E)-2-aryl-1-ethenyl]-4-isoxazolylimino)-1,3-thiazolan-4-ones(3). Mannich reaction of 3 with formaldehyde and secondary amines gave isoxazolyl thiazolidinone Mannich bases (4 and 5).     

Regio-specific synthesis of new 1-(tert-butyl)-1H-pyrazolecarboxamide derivatives

Regio-specific and non-regiospecific condensation reactions on 1,3-dicarbonyl compounds rendered 1,3,5-trisubstituted pyrazoles. Herein, the control of regio-specificity was a significant improvement in pyrazole research. A high yield acylation of poorly nucleophilic aryl amines, which resulted in mono- or diacylated products depending on the reaction conditions, is described. As a result, a library of potentially bioactive compounds was obtained.     

Synthesis and Antimicrobial Activity of Some New 5-(3-Chloro-1-Benzothiophen-2-YL)-1,3,4-Oxadiazole-2-Thiol and Their Derivatives

Abstract

3-Chloro-1-benzothiophene-2-carbonylchloride 1 was made to reacts with hydrazine hydrate afforded 3-chloro-1-benothiophene-2-carbohydrazide 2 in good yield. 5-(3-chloro-1-benzothiophen-2-yl)-1,3,4-oxadiazole-2-thiol 4 was synthesized from 3-chloro-1-benzothiophene-2-carbohydrazide 2. Mannich bases, alkyl halide, and acid chlorides derivatives were then prepared. Compound 4 on condensation with chloroacetone in the presence of NaOH as base and ethanol as solvent gave 1-{[5-(3-chloro-1-benzo[b]thiophen-2-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}propan-2-on 6. Condensation of compound 6 with various aromatic aldehydes afforded a series of chalcones 7a–h. The structures of all the synthesized compounds were confirmed by spectral data and have been screened for antibacterial activity.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

GRAPHICAL ABSTRACT      

Synthesis, crystal and molecular structures, and steroechemical nonrigidity ofN-(chlorodimethylgermylmethyl)-andN-(bromodimethylgermylmethyl)-N-[(S)-1-phenylethyl]acetamides andN-(chlorodimethylgermylmethyl)-4-phenyl-2-pyrrolidone

RacemicN-(chlorodimethylgermylmethyl)-4-phenyl-2-pyrrolidone and the first optically active amide derivatives containing the asymmetrical carbon atom and the five-coordinate germanium atom,viz.,N-(chlorodimethylgermylmethyl)- andN-(bromodimethylgermyl-methyl)-N-[(S)-1-phenylethyl] acetamides, were synthesized. Their structures were established by X-ray diffraction analysis. The geometric characteristics of the trigonal-bipyramidal valence environment about the germanium atoms are compared with those of analogous enantiomeric silicon compounds and the related five-coordinate germanium compounds. The barriers to permutational isomerization of the title compounds were determined by dynamic¹H NMR spectroscopy. It was found that these barriers are higher than those of the corresponding silicon analogs. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 137–144, January, 2000.     

Diversity oriented synthesis of hispanane-like terpene derivatives from (R)-(+)-sclareolide

(R)-(+)-Sclareolide 1 has been used as a starting material to develop a diversity oriented methodology to access hispanane 28 a, and hispanane-like derivatives 27 b-27 e. This methodology is based on the intramolecular Friedel-Crafts acylation of the corresponding 12-desoxylabdanoic-like acids 27, for the construction of the cycloheptane ring which is characteristic of the hispananes. Acids 27 are obtained from alcohols 20, available by addition of the lithium or magnesium reagents to amide 12 (followed by Luche reduction), or to aldehyde 21. This sequence has resulted in the preparation of hispanane framework 27 a. The versatility of this methodology therefore allows a structural diversity oriented synthesis, since it allows the access to a wide variety of hispanane-like derivatives.     

含1-[二-(4-氟苯)甲基]哌嗪均三氮唑环的Mannich碱的合成及表征

微波辐射下,在冰醋酸中,3-甲基-4-氨基-1,2,4-三氮唑-5-硫酮1与芳香醛经微波辐射制得相应的中间体Schiff碱2(a~j),然后中间体2与1-[二-(4-氟苯)甲基]哌嗪于室温反应制得10个新的Mannich碱3(a~j).合成的10个目标化合物通过熔点测定和质谱、红外光谱、核磁共振氢谱分析、元素分析对其结构进行确证。     

Simple One-Pot Synthesis of New Derivatives of the Macrocyclic Aminal 1,3,7,9,13,15,19,21-Octaazapentacyclo-[19.3.1.13,7.19,13.115,19]octacosane (OAPO)

A series of 2,2′-(dihydropyrimidine-1,3(2H,4H)-diyldimethanediyl)bis(substituted-phenols) was synthesized using a Mannich-type reaction between the macrocyclic aminal 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosane (OAPO) (1) and substituted phenols in basic media. These previously unreported compounds were separated from the reaction mixture by column chromatography in highly pure form with 25–75% yields. The most stable conformer was predicted using AM1-type semiempirical quantum chemical calculations.     

Synthesis and properties of <Emphasis Type="Italic">N</Emphasis>-(2-ethoxyethyl) piperidine derivatives of anabasine

The synthesis and pharmacological activity of ethers of 1-(2-ethoxyethyl)-4-[3-anabasin-1-yl-1-prop-1-ynyl]piperidin-4-ol were described. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 360–363, July–August, 2007.     

Microwave-promoted solvent-free synthesis of N-(diphenylmethylene)glycine alkyl esters

The efficient synthesis of N-(diphenylmethylene) glycine alkyl esters was achieved for the first microwave irradiation under solvent-free condition,using PEG or quaternary ammonium salts as phase transfer catalysts(PTCs).Under the optimum conditions, N-(diphenylmethylene) glycine alkyl esters were obtained in excellent yields in most cases.     

(R)-3-叔丁基二甲基硅氧丁基苯硫醚的合成方法改进

以4-(二甲氨基)吡啶为催化剂,通过(R)-3-叔丁基二甲基硅氧丁醇与甲磺酰氯之间的改进烷基磺酰化反应得到(R)-3-叔丁基二甲基硅氧丁基甲磺酸酯(2b,收率98%),2b再与苯硫酚钠反应生成(R)-3-叔丁基二甲基硅氧丁基苯硫醚(3,总收率89%)。2和3的结构经1H NMR,IR和MS表征。     

Alkylation and Acylation of 1-(4-Phenylaminophenyl)dihydropyrimidine-2,4-(1H,3H)-diones

The C- and N-substituted derivatives of 1-(4-phenylaminophenyl)dihydropyrimidine-2,4-(1H,3H)-diones have been obtained by alkylation and acylation. The secondary amino group takes part in the acylation reaction, before the amide group of the heterocycle.     

Synthesis and properties ofN-[1-hydroxyimino-2-methyl-1-(2-pyridyl)prop-2-yl]hydroxylamine and heterocyclic derivatives based on it

N-[1-Hydroxyimino-2-methyl-1-(2-pyridyl)prop-2-yl]hydroxylamine, a new representative of the series of α-hydroxylamino oximes, was synthesized. Based on this compounds, 3-imidazoline 3-oxide and 2-imidazoline 3-oxide derivatives, were obtained, and some of their chemical properties were investigated. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 131–136, January, 1997.