Ontology highlight
ABSTRACT:
SUBMITTER: Outlaw VK
PROVIDER: S-EPMC4275132 | biostudies-literature | 2014 Dec
REPOSITORIES: biostudies-literature
Organic letters 20141205 24
Among privileged structures, indoles occupy a central place in medicinal chemistry and alkaloid research. Here we report a flexible and efficient conversion of pyrrole-3-carboxaldehydes to substituted 7-amino-5-cyanoindoles. Phosphine addition to fumaronitrile proceeds with prototropic rearrangement of the initially formed zwitterion to the thermodynamically favored phosphonium ylide, which is poised for in situ Wittig olefination. The predominantly E-alkene product positions the allylic nitrile ...[more]