A tandem decarboxylation and inverse electron-demand Diels–Alder reaction of amino-thiophenecarboxylic acids with 1,3,5-triazines

✍ Scribed by Qun Dang; Edmund Carruli; Feng Tian; Francis W. Dang; Tony Gibson; Wenyu Li; Huachen Bai; Michael Chung; Scott J. Hecker

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 287 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.03.180

✦ Synopsis

The scope of 1,3,5-triazine inverse electron-demand Diels-Alder (IDA) reactions was expanded to include aminothiophenecarboxylic acids as latent dienophiles. A series of 2-amino-3-thiophenecarboxylic acids (1a-d) and a 3-amino-2-thiophenecarboxylic acid (5) were introduced as productive dienophiles in IDA reactions with various 1,3,5-triazines (2a-e). This method is useful for the one-step synthesis of both thieno [2,3-d]pyrimidines and thieno [3,2-d]pyrimidines, which should complement existing methods.