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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 6
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Original Articles

RAPID SYNTHESIS OF 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES UNDER MICROWAVE IRRADIATION

Fouad Bentiss
,
Michel Lagrenée
&
Didier Barbry Université des Sciences et Technologies de Lille, Laboratoire d’Ingénierie Moléculaire, UPRES EA 2699, Villeneuve d’Ascq, F-59655, France
Pages 935-938 | Received 16 Mar 2000, Published online: 09 Nov 2006

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Ali Ramazani, Morteza Rouhani, Fatemeh Zeinali Nasrabadi & Farideh Gouranlou. (2015) Ultrasound-Promoted Three-Component Reaction of N-isocyaniminotriphenyl-phosphorane, (E)-cinnamic Acids, and Biacetyl. Phosphorus, Sulfur, and Silicon and the Related Elements 190:1, pages 20-28.
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MajidM. Heravi, Vahideh Zadsirjan, Khadijeh Bakhtiari & FatemehF. Bamoharram. (2013) One-Pot, Three Component Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles Catalyzed by Heteropolyacid. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry 43:3, pages 259-263.
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Ali Ramazani, Nahid Shajari, Amir Tofangchi Mahyari, Mehdi Khoobi, Yavar Ahmadi & Ali Souldozi. (2010) (N-Isocyanimino)triphenylphosphorane-Mediated, One-Pot, Efficient Synthesis of Sterically Congested 1,1,1-Trifluoro-2-(5-aryl-1,3,4-oxadiazol-2-yl)-2-propanol Derivatives via Intramolecular Aza-Wittig Reaction. Phosphorus, Sulfur, and Silicon and the Related Elements 185:12, pages 2496-2502.
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Ali Ramazani & Ali Souldozi. (2009) (N-Isocyanimino)triphenylphosphorane as an Efficient Reagent for the Synthesis of 1,3,4-Oxadiazoles from 3-Substituted Benzoic Acid Derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements 184:12, pages 3191-3198.
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Ali Ramazani & Ali Souldozi. (2009) The Reaction of (N-Isocyanimino)triphenylphosphorane with Anthranilic Acid Derivatives: One-Pot Synthesis of 2-Substituted 1,3,4-Oxadiazoles via Intramolecular Aza-Wittig Reaction. Phosphorus, Sulfur, and Silicon and the Related Elements 184:9, pages 2344-2350.
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Zheng Li, Yulin Xing, Xuelin Ma, Shuxiu Xiao & Zhong Lu. (2006) Microwave‐Assisted Expeditious Synthesis of Novel Carbazole‐Based 1,3,4‐Oxadiazoles. Synthetic Communications 36:22, pages 3287-3295.
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Articles from other publishers (43)

Marcin Łuczyński & Agnieszka Kudelko. (2023) Microwave-Assisted Synthesis of Unsymmetrical 5-Phenyl-1,3,4-oxadiazoles Containing Bis(carboxymethyl)amino Group. Applied Sciences 13:22, pages 12427.
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Imane Nadi, Marya Bouanis, Khadija Nohair, Abdelhamid Nyassi, Abdelkader Zarrouk, Charafeddine Jama & Fouad Bentiss. (2023) Elaboration and corrosion resistance of self-assembled 2,5-bis(4-pyridyl)− 1,3,4-oxadiazole film on carbon steel: Surface characterisations, electrochemical assessments and surface pre-treatment effect. Materials Today Communications 35, pages 106382.
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Chinnari Lekkala, Varaprasad Bodala, Kumari Yettula, Bharat Kumar Karasala, Rajitha Lakshmi Podugu & Siddaiah Vidavalur. (2022) Copper-Catalyzed One-Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from Arylacetic Acids and Hydrazides via Dual Oxidation . ACS Omega 7:31, pages 27157-27163.
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Yuan Liu, Yunyan Peng, Jun Luo, Jingkai Liu & Xiaoqing Liu. (2020) Investigation on the Effects of Bridging Groups in Aromatic Diphenol-Based Benzoxazines: Curing Reaction and H Bonds. Industrial & Engineering Chemistry Research 59:26, pages 12085-12095.
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M. Bouanis, M. Tourabi, A. Nyassi, A. Zarrouk, C. Jama & F. Bentiss. (2016) Corrosion inhibition performance of 2,5-bis(4-dimethylaminophenyl)-1,3,4-oxadiazole for carbon steel in HCl solution: Gravimetric, electrochemical and XPS studies. Applied Surface Science 389, pages 952-966.
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Trimurtulu KotipalliVeerababurao KavalaAshok KonalaDonala JanreddyChu-Wei KuoChing-Fa Yao. (2016) Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4-Oxadiazole/1,3,4-Oxadiazoline and 1,2,4-Triazole Derivatives from N-Substituted Hydrazides. Advanced Synthesis & Catalysis 358:16, pages 2652-2660.
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Liang Wang, Jing Cao, Qun Chen & Mingyang He. (2015) One-Pot Synthesis of 2,5-Diaryl 1,3,4-Oxadiazoles via Di- tert -butyl Peroxide Promoted N -Acylation of Aryl Tetrazoles with Aldehydes . The Journal of Organic Chemistry 80:9, pages 4743-4748.
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Moha Outirite, Michel Lagrenée, Belkheir Hammouti & Fouad Bentiss. (2013) A rapid and an efficient synthesis for 3,5-disubstituted 1,2,4-oxadiazoles under microwave irradiation. Research on Chemical Intermediates 41:3, pages 1601-1606.
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Xiang-Yuan Fan, Xiao Jiang, Ying Zhang, Zhen-Bang Chen & Yong-Ming Zhu. (2015) Palladium-catalyzed one-pot synthesis of diazoles via tert-butyl isocyanide insertion. Organic & Biomolecular Chemistry 13:41, pages 10402-10408.
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Priyanka Anant More, Balu Laxman Gadilohar & Ganapati Subray Shankarling. (2014) In Situ Generated Cetyltrimethylammonium Bisulphate in Choline Chloride–Urea Deep Eutectic Solvent: A Novel Catalytic System for One Pot Synthesis of 1,3,4-Oxadiazole. Catalysis Letters 144:8, pages 1393-1398.
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Dhanusu Suresh, Kuppusamy Kanagaraj & Kasi Pitchumani. (2014) Microwave promoted one-pot synthesis of 2-aryl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazole derivatives using Al3+-K10 clay as a heterogeneous catalyst. Tetrahedron Letters 55:27, pages 3678-3682.
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Ramil Y. Baiazitov & Scott E. Denmark. 2014. Methods and Applications of Cycloaddition Reactions in Organic Syntheses. Methods and Applications of Cycloaddition Reactions in Organic Syntheses 471 550 .
Ganesh Majji, Saroj Kumar Rout, Srimanta Guin, Anupal Gogoi & Bhisma K. Patel. (2014) Iodine-catalysed oxidative cyclisation of acylhydrazones to 2,5-substituted 1,3,4-oxadiazoles. RSC Advances 4:11, pages 5357.
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Huan-Yue Ma, Zheng-Gen Zha, Zhen-Lei Zhang, Li Meng & Zhi-Yong Wang. (2013) Electrosynthesis of oxadiazoles from benzoylhydrazines. Chinese Chemical Letters 24:9, pages 780-782.
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Guda Mallikarjuna Reddy, Putta Ramachandra Reddy, Venkatapuram Padmavathi & Adivireddy Padmaja. (2013) Synthesis and Antioxidant Activity of a New Class of Mono‐ and Bis‐Heterocycles. Archiv der Pharmazie 346:2, pages 154-162.
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Z. Ribcovskaia & F. Macaev. (2012) Synthesis of Mono-Substituted and Simmetrically 2, 5-Disubstituted 1, 3, 4-Oxadiazoles. Chemistry Journal of Moldova 7:2, pages 136-142.
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Jian-Quan Weng, Xing-Hai Liu, Hua Huang, Cheng-Xia Tan & Jie Chen. (2012) Synthesis, Structure and Antifungal Activity of New 3-[(5-Aryl-1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol-2(3H)-ones. Molecules 17:1, pages 989-1001.
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Srimanta Guin, Tuhin Ghosh, Saroj Kumar Rout, Arghya Banerjee & Bhisma K. Patel. (2011) Cu(II) Catalyzed Imine C–H Functionalization Leading to Synthesis of 2,5-Substituted 1,3,4-Oxadiazoles. Organic Letters 13:22, pages 5976-5979.
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Ratnadeep S. Joshi, Priyanka G. Mandhane, Wajid Khan & Charansingh H. Gill. (2011) Synthesis and antibacterial activity of novel series of 2‐( p ‐tolyloxy)‐3‐(5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazol‐2‐yl)quinoline . Journal of Heterocyclic Chemistry 48:4, pages 872-876.
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Ali Ramazani, Fatemeh Zeinali Nasrabadi, Asemeh Mashhadi Malekzadeh & Yavar Ahmadi. (2011) Synthesis of sterically congested 1,3,4-oxadiazole derivatives from aromatic carboxylic acids, acenaphthoquinone, and (N-isocyanimino)triphenylphosphorane. Monatshefte für Chemie - Chemical Monthly 142:6, pages 625-630.
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Ali Ramazani, Morteza Rouhani, Aram Rezaei, Nahid Shajari & Ali Souldozi. (2011) The Reaction of ( N ‐Isocyanimino)triphenylphosphorane with Biacetyl in the Presence of Aromatic Carboxylic Acids: Efficient One‐Pot Three‐Component Reaction for the Synthesis of 3‐(5‐Aryl‐1,3,4‐oxadiazol‐2‐yl)‐3‐hydroxybutan‐2‐one Derivatives . Helvetica Chimica Acta 94:2, pages 282-288.
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Ali Ramazani & Aram Rezaei. (2010) Novel One-Pot, Four-Component Condensation Reaction: An Efficient Approach for the Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives by a Ugi-4CR/ aza -Wittig Sequence . Organic Letters 12:12, pages 2852-2855.
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Ali Ramazani, Yavar Ahmadi, Morteza Rouhani, Nahid Shajari & Ali Souldozi. (2010) The reaction of ( N ‐isocyanimino) triphenylphosphorane with an electron‐poor α‐haloketone in the presence of aromatic carboxylic acids: A novel three‐component reaction for the synthesis of disubstituted 1,3,4‐oxadiazole derivatives . Heteroatom Chemistry 21:6, pages 368-372.
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