Application of [3+ 2]-Cycloaddition in the Synthesis of Valdecoxib

…, G Goverdhan, A Sampath, K Mukkanti…

Index: Reddy, Anumula Raghupathi; Goverdhan, Gilla; Sampath, Aalla; Mukkanti, Khagga; Reddy, Padi Pratap; Bandichhor, Rakeshwar Synthetic Communications, 2012 , vol. 42, # 5 p. 639 - 649

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Citation Number: 5

Abstract

Valdecoxib 1 (Fig. 1) is a nonsteroidal anti-inflammatory drug (NSAID), which acts as an inhibitor of cyclooxygenase-2 (COX-2), although in practice it is used for the treatment of rheumatoid arthritis, osteoarthritis, and dysmenorrhea. [ 1–3 View all references ] Several synthetic procedures for valdecoxib 1 are known. Apart from utilizing dipolar cycloaddition, most of the synthetic methods involve either industrially nonviable reagents such as butyl lithium, [ 4 4. Talley , JJ ; ...

Halogenation of vinyl ketoximes. Synthesis of isoxazoles and preparation and silver ion??promoted reactions of 4??halo??2??isoxazolines

[Hansen, John F.; Kim, Yong In; McCrotty, Stephen E.; Strong, Scott A.; Zimmer, Douglas E. Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 475 - 479]

Chemistry of four-membered cyclic nitrones. 3. Reaction with nucleophilic reagents and stereospecific conversion into 1-hydroxyazetidines

[Pennings, Marcel L.M.; Reinhoudt, David N.; Harkema, Sybolt; Hummel, Gerrit J. van Journal of Organic Chemistry, 1982 , vol. 47, # 23 p. 4419 - 4425]