10.3762/bjoc.8.81
The research focuses on the synthesis and coordination behavior of axially chiral oxazoline-carbene ligands with an N-naphthyl framework, specifically their interaction with AuCl·SMe2 to form Au(I) complexes. The main reactants used in the synthesis include methyl 1-hydroxy-2-naphthoate, trifluoromethylation reagents, 2-nitroaniline, Pd/C for reduction, triethyl orthoformate, TsOH for cyclization, and (S)-2-amino-2-phenylethanol, among others. The synthesis process involved several steps, including trifluoromethylation, coupling reactions, reduction, cyclization, and amide formation, leading to the formation of axially chiral ligands. The coordination study with AuCl·SMe2 was conducted using NaOAc in acetonitrile, and the Au(I) complexes were isolated by flash column chromatography. The analysis of the complexes was performed using 1H NMR spectroscopy to compare the chemical shifts of protons on the oxazoline ring before and after complexation, and single-crystal X-ray diffraction studies were employed to confirm the structure of the complexes, revealing a nearly linear coordination geometry around the gold(I) center. The study found that the geometry of the chiral N-naphthyl axis significantly influenced the yields of the Au(I) complexes, with (Sa,S)-7 yielding higher complex yields than (Ra,S)-7.
10.1002/jhet.5570230445
The research details the synthesis of 9-(2-fluorobenzyl)-6-methylamino-9H-purine (1), a novel anticonvulsant agent with potent activity against maximal electroshock-induced seizures in rats and mice. The study explores nine different synthetic routes to compound 1, utilizing various precursors such as 6-chloro-9-(2-fluorobenzyl)-9H-purine (4), 6-methylaminopurine (5), and 9-(2-fluorobenzyl)-1-methyladeninium iodide (8). Key chemicals involved in the synthesis process include 5-amino-4,6-dichloropyrimidine, 2-fluorobenzylamine, ethanol, triethylamine, ethanesulfonic acid, and triethylorthoformate, among others. The preferred route was found to be the condensation of 5-amino-4,6-dichloropyrimidine with 2-fluorobenzylamine, followed by a series of reactions including alkylation, amination, and rearrangement, ultimately yielding the desired compound 1. The conclusions of the research highlight the efficiency and adaptability of the chosen synthetic route for preparing compound 1 and its analogues from readily available starting materials.
10.1016/j.tetlet.2006.04.096
This research article details the one-pot synthesis of quinazolinone derivatives, which are important fused heterocycles with a range of biological activities such as anti-cancer, anti-inflammatory, and anti-malarial properties. The study aimed to develop an efficient method for the synthesis of 4(3H)-quinazolinones using anthranilic acid, trialkyl orthoformate, and amines in the presence of catalysts lanthanum(III) nitrate hexahydrate [La(NO3)3·6H2O] or p-toluenesulfonic acid (PTSA) under solvent-free conditions. The process was found to be simple, efficient, and environmentally friendly, yielding 4(3H)-quinazolinones in a single step with mild catalysts, fast reaction times (5–15 minutes), and excellent yields (82–98%). The chemicals used in the process include anthranilic acid, various substituted alkyl and aryl amines, trimethyl or triethyl orthoformate, and the catalysts La(NO3)3·6H2O or PTSA. The conclusions highlight the advantages of the protocol, such as the solvent-free conditions, simplicity of the experimental procedure, and the high yields obtained, making it a practical alternative to previous methods with environmental and economic considerations.
10.1021/jm00394a017
The research focused on the synthesis and antiviral activity of carbocyclic analogues of xylofuranosides of 2-amino-6-substituted-purines and 2-amino-6-substituted-8-azapurines. The purpose of this study was to explore the potential of these carbocyclic nucleoside analogues as antiviral agents, particularly against herpes simplex virus (HSV-1 and HSV-2), human cytomegalovirus (CMV), and varicella-zoster virus (VZV). The researchers synthesized a series of compounds, including carbocyclic xylofuranosylguanine (C-xylo-G, compound 9) and its 8-aza analogue (compound 13), through a series of chemical reactions involving precursors such as 2-amino-4,6-dichloropyrimidine and 2-azabicyclo[2.2.1]hept-5-en-3-one. The conclusions drawn from the study were that compounds 9 and 13 exhibited significant antiviral activity, with compound 9 being more potent against both HSV-1 and HSV-2. Additionally, compound 9 demonstrated potent activity against CMV and VZV, making it a promising candidate for further in vivo studies. The chemicals used in the synthesis process included various reagents and solvents such as triethyl orthoformate, acetic acid, zinc dust, p-chlorobenzenediazonium chloride, and dimethylformamide, among others.
10.1016/S0014-827X(02)01263-6
The study reports the synthesis and antimicrobial evaluation of novel 7-(4-halophenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene derivatives. The key intermediate, 3-amino-9-chloro-1-(4-halophenyl)-1H-benzo[h]chromene-2-carbonitrile (3), was synthesized by reacting 4-halobenzylidenmalononitriles (1a–c) and ethyl 4-halobenzylidenmalonates (1d–f) with 4-chloro-1-naphthol (2) in an ethanolic piperidine solution. This intermediate was then used to produce a variety of derivatives through reactions with acetic anhydride, benzaldehydes, hydrazine, triethyl orthoformate, and other reagents, resulting in compounds such as 5-chloro-10-methyl-7-(4-halophenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene-8-one (6a–c) and 9-amino-5-chloro-8-imino-7-(4-halophenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene (11a–c). The synthesized compounds were characterized using IR, UV, 1H NMR, and mass spectroscopy. The antimicrobial activity of these compounds was tested against various bacterial and fungal strains, with several compounds showing significant activity. The study highlights the potential of these synthesized compounds as new antimicrobial agents.
10.1248/cpb.21.2146
The study investigates the synthesis and antimicrobial properties of various pyrazolo[1,5-a]pyridine derivatives. The researchers synthesized a series of 2-alkyl-3-acyloxy and 2-alkyl-3-hydroxy pyrazolo[1,5-a]pyridine derivatives using different starting materials and reaction conditions. Key chemicals involved include 1-amino-2-hydroxymethylpyridinium chloride (Ia), acyl anhydrides, benzoyl chloride, and ethyl orthoformate, among others. These chemicals were used to create a range of derivatives through processes such as acylation, hydrolysis, and cyclization. The study also explores the antimicrobial activities of these derivatives, particularly their potential as tuberculostatic agents, with some compounds showing potent inhibitory effects against Mycobacterium tuberculosis. The research provides valuable insights into the chemical synthesis and biological applications of pyrazolo[1,5-a]pyridine derivatives.
10.1021/jm00389a019
The research focused on the synthesis and antiviral evaluation of carbocyclic analogues of 2-amino-6-substituted-purine 3'-deoxyribofuranosides. The purpose of the study was to develop compounds with potential antiviral activity against herpes simplex virus (HSV-1 and HSV-2) and influenza virus. The researchers synthesized a series of carbocyclic analogues, including 3'-deoxyguanosine (3'-CDG), 2-amino-6-chloropurine 3'-deoxyribofuranoside, and 2,6-diamino-8-azapurine 3'-deoxyribofuranoside, among others. The conclusions drawn from the study indicated that 3'-CDG showed significant activity against HSV-1 and HSV-2, with its activity being equal to or greater than that of ara-A, a positive-control drug. However, it was less potent than ara-A and less active than acyclovir. The compound also demonstrated modest activity against influenza virus. The chemicals used in the process included various purine and pyrimidine derivatives, as well as reagents like triethyl orthoformate, hydrochloric acid, and ammonia-methanol for the synthesis of the target compounds. The study also involved the use of analytical techniques such as UV, IR, MS, and NMR for characterization and the assessment of antiviral activity through in vitro tests.
10.1007/BF00842848
The research investigates the reactions of substituted β-amino-α-cyanocrotonamides with ethyl orthoformate and diethylformamide diethylacetal. The purpose is to explore the reaction mechanisms and products formed under different conditions. The study found that when β-cyano-β-amino-α-crotonamide reacts with the diethylacetal of dimethylformamide, it forms 1-benzyl-4-dimethylaminomethylene-5-cyano-1,6-dihydropyrimidin-6-one. However, in the presence of acetic anhydride, the reaction with ethyl orthoformate yields β-cyano-N-benzylethoxymethyleneacetamide instead of a similar pyrimidone. The research concludes that the "hidden" formyl group replaces the "hidden" acetyl group in these reactions, leading to different products. The study provides insights into the specific conditions required for the formation of different products, which could be useful in the synthesis of related compounds.
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