Exquisite Synthesis of a Designed PAR-1 Antagonist

✍ Scribed by Hua-Ming Miao; Gui-Long Zhao; Lin-Shan Zhang; Hua Shao; Jian-Wu Wang

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: German
• Weight: 245 KB
• Volume: 94
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201100128

✦ Synopsis

Abstract

The synthesis of a designed, sterically congested geminal dimethyl‐bearing PAR‐1 antagonist was achieved by a route of ten steps, with the oxidation of an electron‐rich benzaldehyde, the construction of a tertiary alkyl azide, and the selective hydrogenolysis of a 1,5‐fused tetrazole to generate the cyclic amidine with Raney‐Ni being the key steps. The selective hydrogenolysis of 1,5‐fused tetrazole to generate the cyclic amidine with Raney‐Ni was discovered and may be generally used for the synthesis of structurally unusual cyclic amidines. Several unsuccessful attempts to construct the desired geminal dimethyl‐bearing cyclic amidine were also discussed.