Mild and efficient cyanuric chloride catalyzed Pictet-Spengler reaction

作者：Sharma Ashish; Singh Mrityunjay; Rai Nitya Nand; Sawant Devesh^*

来源：Beilstein Journal of Organic Chemistry, 2013, 9: 1235-1242.

DOI：10.3762/bjoc.9.140

• beta-carboline
• cyanuric chloride
• 6-endo cyclization
• Pictet-Spengler
• TCT

A practical, mild and efficient protocol for the Pictet-Spengler reaction catalyzed by cyanuric chloride (trichloro-1,3,5-triazine, TCT) is described. The 6-endo cyclization of tryptophan/tryptamine and modified Pictet-Spengler substrates with both electron-withdrawing and electron-donating aldehydes was carried out by using a catalytic amount of TCT (10 mol %) in DMSO under a nitrogen atmosphere. TCT catalyzed the Pictet-Spengler reaction involving electron-donating aldehydes in excellent yield. Thus, it has a distinct advantage over the existing methodologies where electron-donating aldehydes failed to undergo 6-endo cyclization. Our methodology provided broad substrate scope and diversity. This is indeed the first report of the use of TCT as a catalyst for the Pictet-Spengler reaction.

• 出版日期2013-6-26