1224619-94-6Relevant articles and documents
Synthesis of spirocyclic carbazole- and acridine-lactams
Wuerdemann, Martina,Christoffers, Jens
, p. 1894 - 1898 (2010)
Spirocyclic carbazole- and acridine-lactams were prepared by Fischer-indole or Friedlaender-quinoline synthesis starting from spirocyclic ketones with a lactam ring. All annulation products were obtained as mixtures of separable regioisomers, which differ only in the position of one methyl group. The starting materials were prepared from 2-pyrrolidone and 2-piperidone by a sequence of protection (by N-allylation), α-acylation, iron-catalyzed Michael reaction followed by Robinson-annulation, palladium-catalyzed N-deprotection and catalytic hydrogenation. The overall yields of this six-step sequence are 13 and 17%, respectively, and the racemic ketones are obtained as single diastereoisomers.