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article

Ca(II)-catalyzed, one-pot four component synthesis of functionally embellished benzylpyrazolyl coumarins in water

Srinivasarao Yaragorla, Abhishek Pareek, Ravikrishna Dada, S. Yaragorla, more

Tetrahedron Letters > 2015 > 56 > 33 > 4770-4774

A facile one-pot, four-component synthesis of biologically important benzylpyrazolyl coumarins in water has been demonstrated using environmentally benign Ca(II) as the catalyst. Participation of aliphatic aldehydes has been described for the first time. Short reaction times, high yields and chromatography free isolation of the products, usage of eco-friendly catalyst and solvent are the key features...

article

The syntheses and structures of bis(alkylimino)isoindolines

Ingrid-Suzy Tamgho, James T. Engle, Christopher J. Ziegler, I.S. Tamgho, more

Tetrahedron Letters > 2013 > 54 > 45 > 6114-6117

In this Letter, we present a synthetic and structural study into bis-imino substituted diiminoisoindolines, which can be synthesized either via CaCl ₂ mediated reaction of phthalonitrile with primary amines, or via direct reaction of these amines with unsubstituted diiminoisoindoline. The preferred synthesis does depend on the methodology, and in two cases singly substituted adducts were formed...

article

The medicinal perspective of 2,4‐thiazolidinediones based ligands as antimicrobial, antitumor and antidiabetic agents: A review

Kumari Kajal, Gurpreet Singh, Tathagata Pradhan, Deendyal Bhurta, more

Archiv der Pharmazie > 355 > 9 > n/a - n/a

2,4‐Thiazolidinedione (2,4‐TZD), commonly known as glitazone, is a ubiquitous heterocyclic pharmacophore possessing a plethora of pharmacological activities and offering a vast opportunity for structural modification. The diverse range of biological activities endowed with a novel mode of action, low cost, and easy synthesis has attracted the attention of medicinal chemists. Several researchers have...

article

Synthetic heterocyclic derivatives as promising xanthine oxidase inhibitors: An overview

Gurinder Kaur, Atamjit Singh, Geetakshi Arora, Aditi Monga, more

Chemical Biology & Drug Design > 100 > 3 > 443 - 468

Inhibition of xanthine oxidase (XO) is an effective and most prominent therapeutic approach for the management of gout. Discovery of its association in the pathophysiology of diabetes, cardiovascular disorders, etc., widened its therapeutic horizons. Limited drug candidates in clinical practice along with side effects forced researchers to develop more efficacious and safer XO inhibitors for the management...

article

Applications of medicinal chemistry for drug discovery against Acanthamoeba infections

Usman Ahmed, Ayaz Anwar, Seng‐Kai Ong, Areeba Anwar, more

Medicinal Research Reviews > 42 > 1 > 462 - 512

Acanthamoeba is a genus of free‐living amoebae, pervasively found in the environment. Most of its pathogenic species are the causative agent of sight‐threatening Acanthamoeba keratitis and fatal granulomatous amoebic encephalitis. Despite the advancements in the field of chemotherapy, treating Acanthamoeba infections is still challenging due to incomplete knowledge of the complicated pathophysiology...

article

Fe₃O₄@SiO₂@D‐NHCS‐Tr as an efficient and reusable catalyst for the synthesis of indol‐3‐yl‐4H‐chromene via a multi‐component reaction under solvent‐free conditions

Robabeh Baharfar, Sahar Peiman, Behrooz Maleki

Journal of Heterocyclic Chemistry > 58 > 6 > 1302 - 1310

Fe₃O₄@SiO₂@D‐NHCS‐Tr was used as an efficient catalyst in the three‐component reaction between indole derivatives, salicylaldehyde, and active methylene compounds under solvent‐free conditions to the synthesis of indol‐3‐yl‐4H‐chromene derivatives. The features of this method include the green conditions of the reaction, easy separation, eco‐friendly and cost‐effectiveness of the catalyst, and high...

article

Front Cover Picture: Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols (Adv. Synth. Catal. 4/2021)

Xian‐Rong Song, Ruchun Yang, Qiang Xiao

Advanced Synthesis & Catalysis > 363 > 4 > 851 - 851

The front cover picture illustrates the cascade cyclization of propargylic alcohols with diverse nucleophiles for the construction of heterocyclic compounds via the allenyl carbocation intermediate. In this review, these reactions can be divided into four categories based on the types of nucleophiles, such as C‐nucleophiles, O,S‐nucleophiles, N,P‐nucleophiles, and halo‐nucleophiles. A series of functionalized...

article

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

Xian‐Rong Song, Ruchun Yang, Qiang Xiao

Advanced Synthesis & Catalysis > 363 > 4 > 852 - 876

Heterocyclic compounds are important organic compounds and have emerged as key scaffolds in numerous drugs, natural products, vitamins, biologically and pharmaceutically active compounds. Over the past few decades, the development of versatile methodologies employing propargylic alcohols as synthons for the construction of heterocyclic skeletons has attracted great attention from synthetic chemists...

article

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

Yulia Volkova, Sergey Baranin, Igor Zavarzin

Advanced Synthesis & Catalysis > 363 > 1 > 40 - 61

In recent years, the transition‐metal catalyzed three‐component coupling of an aldehyde, an alkyne and an amine, commonly called A³ coupling has become a powerful tool in organic synthesis. The aim of this review is to give a general overview of A³ coupling utility in the synthesis of heterocycles, highlighting the variety of compounds that can be directly accessed from single reactions. The diverse...

article

[4+2]‐Cycloaddition of para‐Quinone Methides with Hexahydro‐1,3,5‐Triazines: Access to 1,3‐Benzoxazine Derivatives

Xiao Cheng, Shuang‐Jing Zhou, Guo‐Yong Xu, Long Wang, more

Advanced Synthesis & Catalysis > 362 > 3 > 523 - 527

A [4+2]‐cycloaddition of para‐quinone methides with hexahydro‐1,3,5‐triazines is reported. The reaction occurs under very mild conditions (catalyst‐, ligand‐, and base‐free), exhibits a broad substrate scope and excellent functional group tolerance, and affords a series of biologically important 1,3‐benzoxazine derivatives in good to excellent yields. Moreover, the successful late‐stage functionalization...

article

Asymetryczna aminokataliza : użyteczne narzędzie w tworzeniu chemicznej różnorodności

Anna Skrzyńska, Artur Przydacz, Mateusz Dyguda, Aleksandra Topolska, more

Wiadomości Chemiczne > 2020 > [Z] 74, 3-4 > 255--284

Over the last 20 years asymmetric aminocatalysis has emerged as highly useful and reliable method of asymmetric synthesis. It involves the use of primary or secondary amines as catalysts of various stereoselective transformations of carbonyl substrates. Owing to the diverse activation strategies available in asymmetric aminocatalysis, it became a method of choice when the functionalization of prochiral...

article

Synthetic Transformations of Higher Terpenoids. 38.^* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids

M. A. Gromova, Yu. V. Kharitonov, T. V. Rybalova, E. E. Shul’ts

Chemistry of Natural Compounds > 2019 > 55 > 5 > 871-877

The synthesis and properties of tricyclic pimaranes containing a C-16 β-carboline are reported. A Pictet–Spengler reaction of methyl 15-oxo-16-formylisopimarate (prepared in situ from the 15-oxo-15,16-dihydroisopimarate) and tryptamine or tryptophan methyl ester in the presence of trifluoroacetic acid formed a mixture of terpenoid 1,2,3,4-tetrahydro-β-carbolines, 3,4-dihydro-β-carbolines, and β-carbolines...

article

Reaction of phenyl-containing N-substituted 1,3-oxazolidines and 1,3-oxazinanes with triammine(tricarbonyl)chromium

A. N. Artemov, E. V. Sazonova, N. A. Aksenova, G. K. Fukin, more

Russian Chemical Bulletin > 2019 > 68 > 8 > 1548-1554

New heterocyclic compounds with phenyl chromium tricarbonyl substituents were synthesized by the reaction of triammine(tricarbonyl)chromium with phenyl-substituted 1,3-oxazacy-cloalkanes bearing acetyl, tert-butyloxycarbonyl, or phenyl group at the nitrogen atom. The resulting compounds were isolated in the individual state and characterized by physicochemical methods of analysis.

article

Synthesis and Structure of 4-Het(aryl)-3,5,5-trimethoxycarbonyl-2-pyrrolidones

N. V. Gorodnicheva, E. S. Ostroglyadov, O. S. Vasil’yeva, S. V. Makarenko

Russian Journal of General Chemistry > 2019 > 89 > 7 > 1541-1544

Condensation of 2-het(aryl)-1,1-dimethoxycarbonylethenes with acetylaminomalonic acid ester afforded (3R*,4S*)-4-(4-methoxyphenyl)-, (3R*,4S*)-4-(3,4-methylenedioxyphenyl)-, (3R*,4S*)-4-(4-dimethylaminophenyl)-, (3R*,4S*)-4-(2-furyl)-, (3R*,4S*)-4-(indol-3-yl)-, (3R*,4S*)-4-(1-methylindol-3-yl)-, and (3R*,4S*)-4-(1-benzylindol-3-yl)-3,5,5-tris(methoxycarbonyl)-2-pyrrolidones.

article

Synthesis of heterocyclic compounds based on oxamic acid monothiooxamides and thiohydrazides

M. M. Krayushkin, V. N. Yarovenko, I. V. Zavarzin

Russian Chemical Bulletin > 2019 > 68 > 6 > 1143-1163

The review integrates and systematizes the key chemical transformations of monothiooxamides and thiohydrazides of oxamic acids and their derivatives, which give rise to various five-, six-, and seven-membered heterocyclic compounds with several heteroatoms.

article

Synthesis and analgesic activity of octahydro-2H-chromenols, derivatives of aliphatic ketones

I. V. Il’ina, D. V. Korchagina, E. A. Morozova, T. G. Tolstikova, more

Russian Chemical Bulletin > 2019 > 68 > 5 > 1061-1066

A series of compounds with a hydrogenated 2H-chromene skeleton was synthesized by the reaction of ketones and available para-menthane monoterpenoid (—)-isopulegol. A condensation product of (—)-isopulegol with the monoterpene ketone l-menthone was synthesized for the first time. The synthesized heterocycles were tested for analgesic activity and compounds with high analgesic activity in the in vivo...

article

The effect of the structure of derivatives of nitrogen-containing heterocycles on their anti-influenza activity

Tatyana L. Gridina, Alla S. Fedchuk, Stephan S. Basok, Anatoliy G. Artemenko, more

Chemistry of Heterocyclic Compounds > 2019 > 55 > 4-5 > 455-462

An adequate QSAR model based on the simplex representation of the molecular structure was built in order to optimize the search for new anti-influenza agents. Structural interpretation of the model allowed us to identify molecular fragments that determine the activity of compounds against human influenza viruses. Further virtual screening and targeted synthesis allowed us to select a group of potentially...

article

Emerging Trends in the Syntheses of Heterocycles Using Graphene-based Carbocatalysts: An Update

Sharoni Gupta, Rukhsar Banu, Chetna Ameta, Rakshit Ameta, more

Topics in Current Chemistry > 2019 > 377 > 3 > 1-62

Graphene-based carbocatalysts owing to numerous amazing properties such as large specific surface area, high intrinsic mobility, excellent thermal and electrical conductivities, chemical stability, ease of functionalization, simple method of preparation, effortless recovery and recyclability have gained a superior position amongst the conventional homogeneous and heterogeneous catalysts. In this review,...

article

Recent Advances in the A³ Coupling Reactions and their Applications

Irfana Jesin, Ganesh Chandra Nandi

European Journal of Organic Chemistry > 2019 > 16 > 2704 - 2720

Propargylamines are an important class of organic compounds that have been widely used as building blocks for the synthesis of various kinds of chemically and biologically relevant compounds. Over the last few years, there have been a rapid growth in the research dedicated to developing the synthetic protocol for propargylamine derivatives. Among various methods that are reported for the synthesis...

article

Exploration of tautomerizations of succinimide and maleimide assisted by ammonia and methanol: a theoretical perspective

Subhendu Sarkar, Tamalika Ash, Tanay Debnath, Abhijit K. Das

Theoretical Chemistry Accounts > 2019 > 138 > 4 > 1-10

Tautomerizations of succinimide (2,5-pyrrolidinedione) and maleimide (2,5-pyrroledione) assisted by ammonia and methanol molecules have been studied at density functional theory level in aqueous medium implementing polarizable continuum model. Tautomerisms observed in succinimide are keto–enol and amine–imine, but maleimide shows only amine–imine tautomerization. The relative energies (E_rs) of various...

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Ca(II)-catalyzed, one-pot four component synthesis of functionally embellished benzylpyrazolyl coumarins in water

The syntheses and structures of bis(alkylimino)isoindolines

The medicinal perspective of 2,4‐thiazolidinediones based ligands as antimicrobial, antitumor and antidiabetic agents: A review

Synthetic heterocyclic derivatives as promising xanthine oxidase inhibitors: An overview

Applications of medicinal chemistry for drug discovery against Acanthamoeba infections

Fe₃O₄@SiO₂@D‐NHCS‐Tr as an efficient and reusable catalyst for the synthesis of indol‐3‐yl‐4H‐chromene via a multi‐component reaction under solvent‐free conditions

Front Cover Picture: Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols (Adv. Synth. Catal. 4/2021)

Recent Advances in the Synthesis of Heterocyclics via Cascade Cyclization of Propargylic Alcohols

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

[4+2]‐Cycloaddition of para‐Quinone Methides with Hexahydro‐1,3,5‐Triazines: Access to 1,3‐Benzoxazine Derivatives

Asymetryczna aminokataliza : użyteczne narzędzie w tworzeniu chemicznej różnorodności

Synthetic Transformations of Higher Terpenoids. 38.^* Synthesis of Conjugates Containing β-Carboline and Tricyclic Diterpenoids

Reaction of phenyl-containing N-substituted 1,3-oxazolidines and 1,3-oxazinanes with triammine(tricarbonyl)chromium

Synthesis and Structure of 4-Het(aryl)-3,5,5-trimethoxycarbonyl-2-pyrrolidones

Synthesis of heterocyclic compounds based on oxamic acid monothiooxamides and thiohydrazides

Synthesis and analgesic activity of octahydro-2H-chromenols, derivatives of aliphatic ketones

The effect of the structure of derivatives of nitrogen-containing heterocycles on their anti-influenza activity

Emerging Trends in the Syntheses of Heterocycles Using Graphene-based Carbocatalysts: An Update

Recent Advances in the A³ Coupling Reactions and their Applications

Exploration of tautomerizations of succinimide and maleimide assisted by ammonia and methanol: a theoretical perspective

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