Improved method for the preparation of oxadiazoles from diacyl hydrazines

Synthetic Communications

Volumn 40, Issue 20, 2010, Pages 3021-3026

  Ellis, David ^a   Johnson, Patrick S ^a   Nortcliffe, Andrew ^a   Wheeler, Simon ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Cyclization; dehydration; oxadiazoles

Indexed keywords

1 METHYLIMIDAZOLE; HYDRAZINE DERIVATIVE; OXADIAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COST; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 77956913138     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903353721     Document Type: Article

References (22)

1. Warren, R.; Liu, G. ZD4054: A specific endothelin A receptor antagonist with promising activity in metastatic castration-resistant prostate cancer. Exper. Op. Invest. Drugs 2008, 17, 1237.
2. Summa, V.; Petrocchi, A.; Bonelli, F.; Crescenzi, B.; Donghi, M.; Ferrara, M.; Fiore, F.; Gardelli, C.; Gonzalez Paz, O.; Hazuda, D. J.; Jones, P.; Kinzel, O.; Laufer, R.; Monteagudo, E.; Muraglia, E.; Nizi, E.; Orvieto, F.; Pace, P.; Pescatore, G.; Scarpelli, R.; Stillmock, K.; Witmer, M. V.; Rowley, M. Discovery of raltegravir, a potent, selective, orally bioavailable HIV-integrase inhibitor for the treatment of HIV-AIDS infection. J. Med. Chem. 2008, 51, 5843.
3. For example, sulfuric acid, as exemplified in Libman, D. D.; Slack, R. Congeners of pyridine-4-carboxyhyrazide, part 1: Derivatives of 4-cyanopyridine and 2-cyanothiazole. J. Chem. Soc. 1956, 2253, and PPA
4. Komaraiah, A.; Sailu, B.; Reddy, P. S. N. Synthesis of some novel 1,3,4-oxadiazol-2-yl-4(3H)-quinazolinones. Synth. Commun. 2008, 38, 114.
5. Rigo, B.; Couturier, D. Studies on pyrrolidinones: A convenient synthesis of 2-methyl-5- (5-oxo-1-benzyl-2-pyrrolidinyl)-1,3,4-oxadiazole. J. Heterocycl. Chem. 1986, 23, 253 (methane sulfonic acid in combination with P2O5)
6. Rigo, B.; Cauliez, P.; Fasseur, D.; Couturier, D. Acid-catalysed cyclization of bis silyl diacylhydrazines: A new 1,3,4-oxadiazole synthesis. Synth. Commun. 1988, 18, 1247 (triflic acid with Me2SiCl2).
7. Exemplified in Alker, D.; Campbell, S. F.; Cross, P. E.; Burges, R. A.; Carter, A. J.; Gardiner, D. G. Long-acting dihydropyridine calcium antagonists, 3: Synthesis and structure-activity relationships for a series of 2-[(heterocycllmethoxy)methyl] derivatives. J. Med. Chem. 1989, 32, 2381.
8. Verkoyen, C.; Rademacher, P. Synthesis of b-thiolactams and reduction with Raney nickel. Chem. Ber. 1985, 118, 653.
9. Sitzmann, M. E. 1,3,4-Oxadiazoles with SF5-containing substituents. J. Fluorine Chem. 1995, 70, 31.
10. For leading references, consult Yang, Y.-H.; Shi, M. Halogen effects in Robinson- Gabriel-type reaction of cyclopropanecarboxylic acid N0-substituted hyrazides with PPh3=CX4. Tetrahedron Lett. 2005, 46, 6285.
11. James, C. A.; Poirier, B.; Grisé, C.; Martel, A.; Ruediger, E. H. General synthesis of tetrasubstituted alkenyl-1,3,4-oxadiazoles. Tetrahedron Lett. 2006, 47, 511.
12. Hobbs, C. J.; Lynch, R.; Mellor, S. L.; Radford, F.; Gilbert, J. C.; Stokes, S.; Glen, A.; Fuimana, A.; Earnshaw, C. G.; Knutsen, L. J. S.; Dean, K. E. S. Acyclic sulfonamides. WO Patent 2006=030211, 2006.
13. Nishiyama, A.; Bougauchi, M.; Kuroita, T.; Minoguchi, M.; Morio, Y.; Kanzaki, K. Phenoxypropylamine compounds as 5-HTreuptake inhibitors and their preparation, pharmaceutical compositions, and use in the treatment of depression. US Patent 2001=990389, 2001.
14. Wang, Y.; Sauer, D. R.; Djuric, S. W. A simple and efficient one-step synthesis of 1,3,4-oxadiazoles utilizing polymer-supported reagents and microwave heating. Tetrahedron Lett. 2006, 47, 105.
15. Brain, C. T.; Brunton, S. A. Synthesis of 1,3,4-oxadiazoles using polymer-supported reagents. Synlett 2001, 382. PS-BEMP costs ?11 g-1 at a reagent loading of 2.2 mmol g-1; the unsupported reagent retails at ?35 g-1 (Aldrich 2009-2010 prices).
16. For example, Ersmark, K.; Nervall, M.; Hamelink, E.; Janka, L. K.; Clemente, J. C.; Dunn, B. M.; Blackman, M. J.; Samuelsson, B.; A ? qvist, J.; Hallberg, A. Synthesis of malarial plasmepsin inhibitors and prediction of binding modes by molecular dynamics simulations. J. Med. Chem. 2005, 48, 6090.
17. Polymer-supported version: Brain, C. T.; Paul, J. M.; Loong, Y.; Oakley, P. J. Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions. Tetrahedron Lett. 1999, 40, 3275.
18. Sharma, G. V. M.; Begum, A.; Rakesh, K. P. R. Zirconium(IV) chloride-mediated cyclodehydration of 1,2-diacylhydrazines: A convenient synthesis of 2,5-diaryl 1,3,4- oxadiazoles. Synth. Commun. 2004, 34, 2387.
19. Lutun, S.; Hasiak, B.; Couturier, D. A new synthesis of 1,3,4-oxadiazoles: Cyclization of N,N0-diacylhyrazines catalyzed by palladium(O). Synth. Commun. 1999, 29, 111.
20. Rigo, B.; Cauliez, P.; Fasseur, D.; Couturier, D. Reaction of hexamethyldisilazane with diacylhydrazines: An easy 1,3,4-oxadiazole synthesis. Synth. Commun. 1986, 16, 1665.
21. Isobe, T.; Ishikawa, T. 2-Chloro-1,3-dimethylimidazolinium chloride, 2: Its application to the construction of heterocycles through dehydration reactions. J. Org. Chem. 1999, 64, 6989.
22. Liras, S.; Allen, M. P.; Segelstein, B. E. A mild method for the preparation of 1,3,4- oxadiazoles: Triflic anhydride-promoted cyclization of diacylhydrazines. Synth. Commun. 2000, 30, 437.