Denitrative imino-diaza-Nazarov cyclization: synthesis of pyrazoles

An iodine-catalyzed denitrative imino-diaza-Nazarov cyclization (DIDAN) methodology has been developed for the synthesis of pyrazoles with high to excellent yields by using alpha-nitroacetophenone derivatives andin situgenerated hydrazones. The key transformation of this oxidative 4 pi-electrocyclization proceeds through an enamine-iminium ion intermediate. This rapid one-pot DIDAN protocol results in the selective generation of C-C and C-N bonds and cleavage of a C-N bond.