Improved synthesis of valsartan via nucleophilic aromatic substitution on aryloxazoline

Synthetic Communications

Volumn 39, Issue 21, 2009, Pages 3880-3887

  Ghosh, Samir ^a   Kumar, A Sanjeev ^a   Soundararajan, R ^a   Mehta, G N ^a  

^a SARDAR VALLABHBHAI NATIONAL INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Antihypertensive therapy; Nucleophilic aromatic substitution; Oxazoline; Valsartan

Indexed keywords

2 ((2' (4,4 DIMETHYL 4,5 DIHYDRO OXAZOL 2 YL) BIPHENYL 4 YLMETHYL) AMINO) 3 METHYL BUTYRIC ACID METHYL ESTER; 2 ((2' (4,4 DIMETHYL 4,5 DIHYDRO OXAZOL 2 YL) BIPHENYL 4 YLMETHYL) PENTANOYL AMINO) 3 METHYL BUTYRIC ACID METHYL ESTER; 2 [(2' CYANO BIPHENYL 4 YLMETHYL) PENTANOYL AMINO] 3 METHYL BUTYRIC ACID METHYL ESTER; 2' (4,4 DIMETHYL 4,5 DIHYDRO OXAZOL 2 YL) BIPHENYL 4 CARBALDEHYDE; NUCLEOPHILE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; VALSARTAN;

ANTIHYPERTENSIVE THERAPY; AROMATIZATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

EID: 70349921298     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902840819     Document Type: Article

References (11)

1. Duncia, J. V.; Chiu, A. T.; Carini, D. J.; Gregory, G. B.; Johnson, A. L.; Price, W. A.; Wells, G. J.; Wong, P. C.; Calabrese, J. C.; Timmermans, P. B. M. W. M. The discovery of potent nonpeptide angiotensin II receptor antagonists: A new class of potent antihypertensives. J. Med. Chem. 1990, 33, 1312.
2. Wyvratt, M. J.; Patchett, A. A. Recent developments in the design of angiotensin-converting enzyme inhibitors. Med. Res. Rev. 1985, 5, 483.
3. Bühlmayer, P.; Furet, P.; Criscione, L.; de Gasparo, M.; Whitebread, S.; Chmidlin, T.; Lattmann, R. Wood. Valsartan, a potent, orally active angio-tensin II antagonist developed from the structurally new amino acid series. J. Bioorg. Med. Chem. Lett. 1994, 4, 29.
4. Carini, D.; Duncia, J.; Aldrich, P.; Chiu, A.; Johnson, A.; Pierce, M.; Price, W.; Santella III, J.; Wells, G.; Wexler, R.; Wong, P.; Yoo, S. E.; Timmermans, P. Nonpeptide angiotensin II receptor antagonist: The discovery of a series of N-(biphenyl methyl)imidazoles as potent, orally active anti-hypertensives. J. Med. Chem. 1991, 34, 2525-2547.
5. Negishi, E.; King, A. O.; Okukado, N. Selective carbon-carbon bond formation via transition metal catalysis, 3: A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel-or palladium-catalyzed reaction of aryl-and benzylinic derivatives with aryl halides. J. Org. Chem. 1977, 42, 1821-1823.
6. Fanta, P. E. The Ullmann synthesis of biaryls, 1945-1963. Chem. Rev. 1964, 64, 613-632.
7. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
8. Martins, C. I.; Coelho, P. J.; Carvalho, L. M.; Oliveira-Campos, A. M. F.; Samat, A.; Guglielmetti, R. Photochromic properties of new benzoindene-fused 2H-chromenes. Helv. Chim. Acta 2003, 86, 570-578.
9. Goossen, L. J.; Melzer, B. Synthesis of valsartan via decarboxylative biaryl coupling. J. Org. Chem. 2007, 72, 7473-7476.
10. Rizzacasa, M. A.; Sargent, M. V. Synthetic approaches to the napthyl-isoquinoline alkaloids, part 1: Dehydroancistrocladisine. J. Chem. Soc., Perkin Trans. 1 1991, 840-844.
11. Dordor, I. M.; Mellor, J. M.; Kennewell, P. D. Reaction of oxazolines with phosphorous oxychloride. J. Chem. Soc., Perkin Trans. 1 1984, 1253-1258.