An efficient synthesis of substituted hexahydrobenzo[f]thieno[c]quinoline; an advanced intermediate of analog of A-86929, a dopamine D1 full agonist

Abstract

An efficient synthesis of substituted hexahydrobenzo[f]thieno[c]quinolines was achieved via catalytic one-pot aziridination followed by Friedel–Crafts cyclization and a mild Pictet–Spengler cyclization protocol. Cu(OTf)2 was an effective catalyst for both aziridination followed by Friedel–Crafts cyclization with excellent diastereoselectivity (dr: >99: 1) and high yield (75%).