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Utility of p-nitrophenyl 3-bromo-2,2-diethoxypropionate (NPBDP) in heterocyclic synthesis

Cite this: J. Org. Chem. 1984, 49, 25, 4800–4805
Publication Date (Print):December 1, 1984
https://doi.org/10.1021/jo00199a010
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    Cited By

    This article is cited by 33 publications.

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    7. A. G. M. Barrett,, B. T. Hopkins, and, J. Köbberling. ROMPgel Reagents in Parallel Synthesis. Chemical Reviews 2002, 102 (10) , 3301-3324. https://doi.org/10.1021/cr0103423
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    13. Nageswara Kode, Jean Vanden Eynde, Annie Mayence, Guangdi Wang, Tien Huang. Design and Synthesis of N1,N5-bis[4-(5-Alkyl-1,2,4-oxadiazol-3-yl)phenyl]glutaramides as Potential Antifungal Prodrugs. Molecules 2013, 18 (9) , 11250-11263. https://doi.org/10.3390/molecules180911250
    14. Babak Kaboudin, Leila Malekzadeh. Organic reactions in water: an efficient method for the synthesis of 1,2,4-oxadiazoles in water. Tetrahedron Letters 2011, 52 (48) , 6424-6426. https://doi.org/10.1016/j.tetlet.2011.09.081
    15. Shahnaz Rostamizadeh, Hamid Reza Ghaieni, Reza Aryan, Ali-Mohammad Amani. One-Pot Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles Directly from Nitrile and Hydroxylamine Hydrochloride Under Solvent-Free Conditions Using Potassium Fluoride as Catalyst and Solid Support. Synthetic Communications 2010, 40 (20) , 3084-3092. https://doi.org/10.1080/00397910903370642
    16. Shahnaz Rostamizadeh, Hamid Reza Ghaieni, Reza Aryan, Ali Mohammad Amani. Clean one-pot synthesis of 1,2,4-oxadiazoles under solvent-free conditions using microwave irradiation and potassium fluoride as catalyst and solid support. Tetrahedron 2010, 66 (2) , 494-497. https://doi.org/10.1016/j.tet.2009.11.063
    17. Ganesh R. Jadhav, Mohammad U. Shaikh, Rajesh P. Kale, Anand R. Ghawalkar, Charansingh H. Gill. Synthesis, characterization, and antimicrobial activities of clubbed [1,2,4]‐oxadiazoles with fluorobenzimidazoles. Journal of Heterocyclic Chemistry 2009, 46 (5) , 980-987. https://doi.org/10.1002/jhet.177
    18. Frank W. Foss, Thomas P. Mathews, Yugesh Kharel, Perry C. Kennedy, Ashley H. Snyder, Michael D. Davis, Kevin R. Lynch, Timothy L. Macdonald. Synthesis and biological evaluation of sphingosine kinase substrates as sphingosine-1-phosphate receptor prodrugs. Bioorganic & Medicinal Chemistry 2009, 17 (16) , 6123-6136. https://doi.org/10.1016/j.bmc.2009.04.015
    19. Rajesh O. Bora, Mazahar Farooqui. Synthesis of substituted 1,2,4‐oxadiazoles from substituted acid chlorides and amidoximes under mild conditions. Journal of Heterocyclic Chemistry 2007, 44 (3) , 645-649. https://doi.org/10.1002/jhet.5570440321
    20. Babak Kaboudin, Fariba Saadati. Magnesia-supported hydroxylamine hydrochloride in the presence of sodium carbonate as an efficient reagent for the synthesis of 1,2,4-oxadiazoles from nitriles. Tetrahedron Letters 2007, 48 (16) , 2829-2832. https://doi.org/10.1016/j.tetlet.2007.02.105
    21. Babak Kaboudin, Fariba Saadati. Novel method for the synthesis of 1,2,4-oxadiazoles using alumina supported ammonium fluoride under solvent-free condition. Journal of Heterocyclic Chemistry 2005, 42 (4) , 699-701. https://doi.org/10.1002/jhet.5570420434
    22. Babak Kaboudin, Kian Navaee. One-Pot Synthesis of 1,2,4-Oxadiazoles Mediated by Microwave Irradiation under Solvent-Free Condition. HETEROCYCLES 2003, 60 (10) , 2287. https://doi.org/10.3987/COM-03-9769
    23. Renaud Beaudegnies, Sebastian Wendeborn. Synthesis of Furazane Conjugated New Heterocycles. HETEROCYCLES 2003, 60 (11) , 2417. https://doi.org/10.3987/COM-03-9833
    24. Tao Zhou, Zhen-Chu Chen. HYPERVALENT IODINE IN SYNTHESIS. 75. A CONVENIENT SYNTHESIS OF OXADIAZOLES BY PALLADIUM-CATALYZED CARBONYLATION AND CYCLIZATION OF DIARYLIODONIUM SALTS AND AMIDOXIMES. Synthetic Communications 2002, 32 (6) , 887-891. https://doi.org/10.1081/SCC-120002699
    25. François Huet. Ethyl Pyruvate Diethyl Acetal. 2001https://doi.org/10.1002/047084289X.re115
    26. Rébecca F Poulain, André L Tartar, Benoı̂t P Déprez. Parallel synthesis of 1,2,4-oxadiazoles from carboxylic acids using an improved, uronium-based, activation. Tetrahedron Letters 2001, 42 (8) , 1495-1498. https://doi.org/10.1016/S0040-4039(00)02293-0
    27. Suk-Ku Kang, Hyung-Chul Ryu, Young-Taek Hong. Palladium-catalyzed Carbonylative Coupling of Hypervalent Iodonium Salts with Amidoximes: Synthesis of Oxadiazoles. HETEROCYCLES 2001, 54 (2) , 985. https://doi.org/10.3987/COM-00-S(I)16
    28. Jonathan R. Young, Robert J. DeVita. Novel synthesis of oxadiazoles via palladium catalysis. Tetrahedron Letters 1998, 39 (23) , 3931-3934. https://doi.org/10.1016/S0040-4039(98)00719-9
    29. M. Ross Grimmett. Imidazoles. 1996, 77-220. https://doi.org/10.1016/B978-008096518-5.00060-5
    30. . Volume 3 References. 1996, 817-932. https://doi.org/10.1016/B978-008096518-5.00249-5
    31. Willi Kantlehner. Synthesis of Iminium Salts, Orthoesters and Related Compounds. 1991, 485-599. https://doi.org/10.1016/B978-0-08-052349-1.00166-9
    32. John L. LaMattina, Christian J. Mularski, David E. Muse. Synthesis of 2-amino-5-hydroxy-4-pyrimidones and 5,6-biheteroaryls using p-nitrophenyl 3-bromo-2,2-diethoxypropionate (NPBDP). Tetrahedron 1988, 44 (11) , 3073-3078. https://doi.org/10.1016/S0040-4020(01)85939-1
    33. J. L. LAMATTINA, C. J. MULARSKI. ChemInform Abstract: UTILITY OF P‐NITROPHENYL 3‐BROMO‐2,2‐DIETHOXYPROPIONATE (NPBDP) IN HETEROCYCLIC SYNTHESIS. Chemischer Informationsdienst 1985, 16 (19) https://doi.org/10.1002/chin.198519210

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