One-Pot Consecutive Sulfonamidation/ipso-Cyclization Strategy for the Construction of Azaspirocyclohexadienones

Harnessing of Morita-Baylis-Hillman (MBH) carbonates of acetylenic aldehydes as handy synthons has allowed a facile synthesis of azaspirocyclohexadienones by sequential DABCO-promoted sulfonamidation/ICl-mediated ipso-iodocyclization reactions. A variety of MBH-carbonates having aryl or heteroaryl groups on the alkyne functionality fruitfully participated in the one-pot ipso-annulation reaction to provide the corresponding 3-iodo spirocyclohexadienones. The sulphonamide functionality was further utilized to construct the tricyclic fused-sultam framework.