Abstract

A number of highly functionalized Morita–Baylis–Hillman (MBH) adducts have been synthesized from N‐methylisatin and aryl and heteroaryl aldehydes as electrophiles and the less well‐known propargyl, allyl, and tert‐butyl acrylates as labile, activated alkenes in excellent yields. The MBH adducts thus obtained underwent azomethine ylide [3+2] cycloaddition reactions to yield unusual ring‐enlarged, angularly fused pyrrolo[3,2‐c]quinoline lactones in excellent yields. Subsequent reaction of the quinolin‐2‐one lactones under Hoffman elimination conditions (BnBr/KOH) afforded a lactone ring‐opened 4‐carboxy‐3‐vinyl‐1,2‐dihydroquinolin‐2‐one. A plausible mechanism and discussion of the stereochemical aspects of the cycloaddition reaction are provided.

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call

Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.