Base-Mediated Cyclopentannulation of Ynones with Amino Crotonates for Regio- and Stereoselective Synthesis of Pentafulvenes and Cyclopenta[c]quinolines

Abstract

A regio- and stereoselective synthesis of unsymmetrically substituted pentafulvenes is reported via the condensation of readily available ynones and amino crotonates under very mild conditions. The mechanism of this 3 + 2 annulation involved a vinylogous Michael addition followed by an intramolecular enamine aldol condensation. Substrates with o-bromo tether further cyclized to pentannulated hydroquinolines through an isomerization/SNAr in the same reaction pot at the elevated temperature.

An Approach to Functionally Embellished o-Alkynylbenzoates or Furan-3(2H)-ones from Diynones and DMAD: Controlled Divergence and Product Selectivity

“…A fillip to such endeavors in the recent past has come from ready, green access to diynone from ethyl lactate . A selection of the diverse reactivity displayed by diynones, − including contributions from our group, is captured in Scheme to provide a flavor and backdrop to the efforts disclosed in this report.…”