Microwave-Assisted Synthesis of 2,5-Disubstituted-1,3,4-Oxadiazoles

Khan, Khalid Mohammed; Ziaullah,; Rani, Mubeen; Perveen, Shahnaz; Haider, Syed Moazzam; Choudhary, M. Iqbal; Atta-ur-Rahman, _; Voelter, Wolfgang

doi:10.2174/1570178043488608

Cited by 38 publications

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“…The recent role of microwave (MW) irradiation in performing organic reactions [13][14][15][16], attracted our attention to develop its use in our laboratory [17][18][19][20][21][22] and in the present work both of the conventional and MW irradiation conditions were performed to explore the optimum conditions for the synthesis of new benzo [b]thienyl-1,2,4-triazoles and investigating the selectivity encountered on their alkylation. The AM1 calculations [23] were performed, using MOPAC7 program package [24], to explain the regioselectivity of the alkylation reactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and alkylation of 5‐(3‐chlorobenzo[b]thien‐2‐yl)‐4H‐1,2,4‐triazole‐3‐thiol under classical and microwave conditions. AM1 semiemperical calculations for investigating the regioselectivity of alkylation

Ashry

Kassem

Hamid

et al. 2006

Journal of Heterocyclic Chem

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Under microwave irradiation (MWI), 5‐(3‐chlorobenzo[b]thien‐2‐yl)‐4H‐1,2,4‐triazole‐3‐thiol (3) was synthesized in a good yield by intramolecular cyclization of the carbonyl thiosemicarbazide 2. A regioselective S‐alkylation of 3 with benzyl chloride or allyl bromide has been achieved by using triethylamine as a base, while other different basic conditions led to a mixture of bis(alkylated) derivatives N4, S‐ and S, N2‐, under both of classical and MWI conditions. The relative stabilities, charge densities, dipole moments and electronic energies of reactants, transition states and intermediates were calculated by the AM1 method and used for investigating the regioselectivity.

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Section: Introductionmentioning

confidence: 99%

Synthesis and alkylation of 5‐(3‐chlorobenzo[b]thien‐2‐yl)‐4H‐1,2,4‐triazole‐3‐thiol under classical and microwave conditions. AM1 semiemperical calculations for investigating the regioselectivity of alkylation

Ashry

Kassem

Hamid

et al. 2006

Journal of Heterocyclic Chem

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“…The present method is an important addition to MW-assisted synthetic methodologies. [41] Reaction of isonicotinohydrazide with different aromatic aldehydes under MW irradiation gives Schiff's bases. These Schiff's bases were converted into 1,3,4-oxadiazole derivatives by treating with acetic anhydride under the MW irradiation (Scheme 27).…”

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confidence: 99%

Microwave-Assisted Synthesis of Five-MemberedO,N,N-Heterocycles

Kaur

2014

Synthetic Communications

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The development of new strategies for synthesis of five-membered O,N,Nheterocycles has remained a highly attractive but challenging proposition. An overview of the application of microwave irradiation in oxygen and two nitrogen atoms containing five-membered heterocyclic compounds synthesis is presented, focusing on the developments in the past 5-10 years. This contribution covers the literature concerning the total synthesis of five-membered O,N,N-heterocycles.

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“…7) Literature survey reveals that 2,5-disubstituted 1,3,4-oxadiazoles have been synthesized either by thermal/acid catalysed cyclization of 1,2-diacylhydrazines 8) or by oxidative cyclization of semicarbazone/hydrazone in the presence of an oxidant 9) or by microwave irradiation of hydrazide and carboxylic acid mixture. 10) 1,3,4-Thiadiazole nucleus constitutes the active part of several biologically active compounds including antibacterial, antimycotic and anti-inflammatory agents. 11,12) Most frequently used methods for the synthesis of thiadiazoles include the reaction of acylthiosemicarbazides with acid reagents such as trifluoroacetic acid 13) and methanesulfonic acid.…”

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confidence: 99%

Synthesis, Antimicrobial and Cytotoxic Activities of Sulfonamidomethane Linked Heterocycles

Swapna

Reddy

Padmaja

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new class of sulfonamidomethane pyrrolyl-oxadiazoles/thiadiazoles and pyrazolyl-oxadiazoles/ thiadiazoles was prepared from arylsulfonylaminoacetic acid hydrazides and E-cinnamic acid. The lead compounds were tested for antimicrobial and cytotoxic activities. The thiadiazole compounds having chloro substituent on the aromatic ring 4c, 8c and 10c exhibited comparable antibacterial activity against Pseudomonas aeruginosa and also antifungal activity against Penicillium chrysogenum. The styryl oxadiazole compound 3c showed appreciable cytotoxic activity on A549 lung carcinoma cells which can be used as a lead compound in the future studies.

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Microwave-Assisted Synthesis of 2,5-Disubstituted-1,3,4-Oxadiazoles

Cited by 38 publications

References 0 publications

Synthesis and alkylation of 5‐(3‐chlorobenzo[b]thien‐2‐yl)‐4H‐1,2,4‐triazole‐3‐thiol under classical and microwave conditions. AM1 semiemperical calculations for investigating the regioselectivity of alkylation

Synthesis and alkylation of 5‐(3‐chlorobenzo[b]thien‐2‐yl)‐4H‐1,2,4‐triazole‐3‐thiol under classical and microwave conditions. AM1 semiemperical calculations for investigating the regioselectivity of alkylation

Microwave-Assisted Synthesis of Five-MemberedO,N,N-Heterocycles

Synthesis, Antimicrobial and Cytotoxic Activities of Sulfonamidomethane Linked Heterocycles

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