A Short Preparation of Pyrroloquinoxalinones via a Cascade Reaction of N-Aryl-5-alkylamino-2-nitrosoanilines with Methyl 2-Cyanoalkanoates: Unexpected Direction of Nucleophilic Substitution of Hydrogen

作者：Krolikiewicz Magdalena; Cmoch Piotr; Wrobel Zbigniew^*

来源：Synlett, 2013, 24(8): 973-976.

DOI：10.1055/s-0032-1316903

• carbanions
• condensation
• heterocycles
• annulation
• nucleophilic aromatic substitution

N-Aryl-2-nitrosoanilines possessing 5-alkylamino groups undergo a bisheteroannulation reaction with anions of 2-cyanoalkanecarboxylates resulting in pyrroloquinoxalinone derivatives. The cascade reaction involves condensation of the cyanoester anions with the nitroso group, unusual nucleophilic substitution of hydrogen in the nitrosoaniline-derived intermediate with the second carbanion molecule, and double intramolecular acylation of the amino functions.

• 出版日期2013-5