Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

One-Pot Consecutive Sulfonamidation/ipso-Cyclization Strategy for the Construction of Azaspirocyclohexadienones
Santosh Kumar Prajapti, Kamalkishor Warudikar, Ravi Ranjan, Chada Raji Reddy
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01285

DOI: 10.1021/acs.joc.7b01285

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