Convenient Synthesis of Pharmacologically Active Ortho-Substituted Biaryl Oxazolines via the Suzuki Reaction

REFERENCES

• Wexler , R. R. ; Greenlee , W. J. ; Irvin , J. D. ; Goldberg , M. R. ; Prendergast , K. ; Smith , R. D. ; Timmermans , P. B. M. W. M. Nonpeptide angiotensin II receptor antagonists: The next generation in antihypertensive therapy . J. Med. Chem. 1996 , 39 ( 3 ), 625 – 656 .
   PubMed Web of Science ®Google Scholar
• Hauel , N. ; Narr , B. ; Ries , U. ; van Meel , J. C. A. ; Wienen , W. ; Entzeroth , M. Benzimidazoles useful as angiotensin. US Patent 5,591,762, 1997.
   Google Scholar
• Venkataraman , S. ; Mathad , V. T. ; Kikkuru , S. R. ; Neti , S. ; Chinta , R. R. ; Arunagiri , M. ; Routhu , L. Process for preparing the telmisartan. PCT WO Patent 06/044754A2, 2006 .
   Google Scholar
• Reddy , K. S. ; Srinivasan , N. ; Reddy , C. R. ; Kolla , N. ; Anjaneyulu , Y. ; Venkatraman , S. ; Bhattacharya , A. ; Mathad , V. T. An efficient and impurity-free process for telmisartan: An antihypertensive drug . Org. Process Res. Dev. 2007 , 11 ( 1 ), 81 – 85 .
   Web of Science ®Google Scholar
• Marxer , R. ; McKenna , J. M. ; Rodriguez , H. R. ; Tsai , H. M. Synthesis of spiro [isobenzofuran-l (3H),4′-piperidines] and spiro [isobenzofuran-1 (3H),3′-piperidines] . J. Org. Chem. 1975 , 40 ( 10 ), 1427 – 1433 .
   Web of Science ®Google Scholar
• Meyers , A. I. ; Gabel , R. ; Mihelich , E. D. Nucleophilic aromatic substitution on o-(methoxy)aryloxazolines: A convenient synthesis of o-alkyl-, o-alkylidene, and o-arylbenzoic acids . J. Org. Chem. 1978 , 43 , 1372 .
   Web of Science ®Google Scholar
• Meyers , A. I. ; Gabel , R. ; Mihelich , E. D. Nucleophilic aromatic substitution on aryl oxazolines: An efficient approach to unsymmetrically substituted biphenyls and o-alkyl benzoic acids . J. Am. Chem. Soc. 1975 , 10 , 7383 – 7385 .
   Google Scholar
• Ellefson , C. R. ; Prodan , K. A. ; Brougham , L. R. ; Miller , A. Synthesis of 8-aryltetrahydroisoquinolines as dopamine antagonists and evaluation for potential neuroleptic activity. J. Med. Chem. 1980, 23, 977.
   PubMed Web of Science ®Google Scholar
• Seijas , J. A. ; Vázquez-Tato , M. P. ; Martínez , M. M. ; Pizzolatti , M. G. Oxazoline as a useful tool in organic synthesis: Preparation of 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid skeleton . Tetrahedron Lett. 2005 , 46 , 5827 .
   Web of Science ®Google Scholar
• Astley , D. ; Saygi , H. ; Gezer , S. ; Astley , S. T. Uncatalysed coupling of an activated aryl chloride with aryllithium and aryl Grignard reagents . Tetrahedron Lett. 2004 , 45 , 7315 .
   Web of Science ®Google Scholar
• Meyers , A. I. ; Williams , B. E. Oxazolines as activating groups in aromatic substitution nucleophilic displacement of o-fluoro substituents by organometallics and lithio amides . Tetrahedron Lett. 1978 , 19 , 223 – 226 .
   Google Scholar
• Urawa , Y. ; Furukawa , K. ; Shimizu , T. ; Yamagishi , Y. ; Tsurugi , T. ; Ichino , T. Process for preparation of biphenyl containing intermediates useful in making angiotensin II receptor antagonists. US Patent 5,557,002, 1996 .
   Google Scholar