Application of 7-endo-trig Pictet-Spengler Cyclization to the Formation of the Benzazepine Ring: Synthesis of Benzazepinoindoles

作者：Sharma Sudhir K; Sharma Sunil; Agarwal Piyush K; Kundu Bijoy^*

来源：European Journal of Organic Chemistry, 2009, 2009(9): 1309-1312.

DOI：10.1002/ejoc.200801201

• Fused-ring systems
• Nitrogen heterocycles
• Cyclization
• Polycycles

The preparation of benzazepinoindoles, fused heterocycles with a benzazepine moiety, was accomplished through an intramolecular 7-endo-trig Pictet-Spengler cyclization. The precursors comprising C-3- or C-2-linked o-aminobenzylindoles required for the cyclization were obtained either by treating indoles with o-nitrobenzyl bromide followed by reduction of the nitro group or by treating 2-nitrophenylacetic acid with DCC/DMAP followed by reduction of the aryl nitro functionality. Resulting substrates 5 and 6 were then subjected to the 7-endo-trig Pictet-Spengler reaction with a variety of aldehydes and ketones to furnish new polycyclic structures benzazepinoindoles.

• 出版日期2009-3