Thioamides as useful synthons in the synthesis of heterocycles.

Nitrogen‐, and/or Sulfur-Containing Heterocyclic Rings Poulomi Majumdar,†,‡ Anita Pati,†,§ Manabendra Patra, Rajani Kanta Behera,† and Ajaya Kumar Behera*,† †Organic Synthesis Laboratory, School of Chemistry, Sambalpur University, Jyoti Vihar, Burla 768019, Orissa, India ‡State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, 116024, P.R. China School of Applied Sciences (Chemistry), KIIT University, Bhubaneswar 751024, India National Institute of Science & Technology, Palur Hill, Berhampur 761068, Orissa, India

Acid hydrazides, potent reagents for synthesis of oxygen-, nitrogen-, and/or sulfur-containing heterocyclic rings.

This review provides readers with an overview of the main synthetic methodologies for 1,3,4-oxadiazole derivatives, and of their broad spectrum of pharmacological activities as reported over the past twelve years.

https://www.mdpi.com/1420-3049/17/9/10192/pdf

Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012

Design and synthesis of azolopyrimidoquinolines, pyrimidoquinazolines as anti-oxidant, anti-inflammatory and analgesic activities.

The molecular structures and spectral properties of α-haloketones as well as their syntheses are analyzed and reviewed. Their reactivity towards oxygen, nitrogen, and sulfur nucleophiles, carboxylic acids, carbon nucleophiles, alkenes, and alkynes are discussed.

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The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

This study aimed for the synthesis of new heterocyclic compounds incorporating sulfamoyl moiety suitable for use as antimicrobial agents via a versatile, readily accessible N-[4-(aminosulfonyl)phenyl]-2-cyanoacetamide (3). The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with acetylacetone or arylidenes malononitrile. Cycloaddition reaction of cyanoacetamide with salicyaldehyde furnished chromene derivatives. Diazotization of 3 with the desired diazonium chloride gave the hydrazone derivatives 13a–e. Also, the reactivity of the hydrazone towards hydrazine hydrate to give Pyrazole derivatives was studied. In addition, treatment of 3 with elemental sulfur and phenyl isothiocyanate or malononitrile furnished thiazole and thiophene derivatives respectively. Reaction of 3 with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt 17 which reacted in situ with 3-(2-bromoacetyl)-2H-chromen-2-one and methyl iodide afforded the thiazole and ketene N,S-acetal derivatives respectively. Finally, reaction of 3 with carbon disulfide and 1,3-dibromopropane afforded the N-[4-(aminosulfonyl) phenyl]-2-cyano-2-(1,3-dithian-2-ylidene)acetamide product 22. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis. The compounds were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results.

Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety

Superabsorbent hydrogel based on sulfonated-starch for improving water and saline absorbency.

1-(3-Amino-6-methyl-4-pyridin-3-yl-1H-pyrazolo[3,4-b]pyridin-5-yl)ethanone (3) was obtained in very pure state and used as a good starting material for the present study. It diazotized to give the corresponding diazonium salt 9 and also reacted with phenyl isothiocyanate to give the corresponding thiourea derivative 4. Compound 4 was used for the preparation of thiazole derivatives 5–8 via the reaction with active halogen-containing compounds. On the other hand, compound 9 coupled with several active –CH2- containing compounds to afford the corresponding triazine derivatives 10–17. Considering the data from IR, 1 H NMR, mass spectra, and elemental analyses, the chemical structures of the newly synthesized heterocyclic compounds were elucidated. Cytotoxicity, anti-HSV1, and anti-HAV-MBB activity were evaluated for the newly synthesized heterocyclic compounds.

Synthesis, Reactions, and Antiviral Activity of 1-(1H-Pyrazolo[3,4-b]pyridin-5-yl)ethanone and Pyrido[2′,3′:3,4]pyrazolo[5,1-c][1,2,4]triazine Derivatives

The ylidene derivatives of cyanothioacetamide 1a–d reacted with ethyl acetoacetate to give the pyridinethiol derivatives 2a–d. Compounds 2a–d were used as starting material for the synthesis of several heterocyclic compounds. Reactions with hydrazine hydrate, ethyl iodide, methyl chloroacetate and α-chloro ethyl acetoacetate gave the pyridine and annelated pyridine derivatives 5a–d, 6a–d, 7a, 8b–d, and 12a–d, respectively. Compounds 7a, 8b–d and 12a–d reacted with hydrazine hydrate to yield the annelated pyridines 10a–d and 15a–d, respectively.

Reactions with cyanothioacetamide derivatives : synthesis and reactions of some pyrazolo[3,4-b]pyridine derivatives

The pyrazolopyridine derivatives 1a,b reacted with phenylisothiocyanate (2), nitrous acid and cinnamonitrile derivatives 5a,b to afford the corresponded pyrazolo[3,4-b]-pyridinyl-3-phenylthiourea derivatives 3a,b, 3-diazotized aminopyrazolo[3,4-b]-pyridine derivatives 4a,b and Schiff bases 7a-d in a respective manner. Compounds 3a,b, 4a,b and 7a,d were taken as the starting materials for the present study owing to the presence of more than one active site. Compounds 3a,b reacted with the halogen-containing reagents e.g. 11a,b, 13 and 15 to give the corresponded thiazole derivatives 12a-d, 14a,b and 16a,b respectively. Compounds 4a,b coupled with the active hydrogen-containing reagents 17a,j to afford the corresponding 3-hydrazino derivatives 18a-t which could be cyclized to give the corresponding triazines 19a-t respectively. Compounds 7a-d reacted with thioglycolic acid (9) to give the corresponding thiazole derivative 10a-d in a good yield. The assigned structures of the newly synthesized compo...

Fawzy A. Attaby

Papers

Synthesis and Antimicrobial Evaluation of Some Novel Thiazole, Pyridone, Pyrazole, Chromene, Hydrazone Derivatives Bearing a Biologically Active Sulfonamide Moiety

Superabsorbent hydrogel based on sulfonated-starch for improving water and saline absorbency.

Synthesis, Reactions, and Antiviral Activity of 1-(1H-Pyrazolo[3,4-b]pyridin-5-yl)ethanone and Pyrido[2′,3′:3,4]pyrazolo[5,1-c][1,2,4]triazine Derivatives

Reactions with cyanothioacetamide derivatives : synthesis and reactions of some pyrazolo[3,4-b]pyridine derivatives

Synthesis of Thiazole, Triazole, Pyrazolo[3,4-b]-Pyridinyl-3-Phenylthiourea, Aminopyrazolo[3,4-b]Pyridine Derivatives and Their Biological Evaluation