One-Step Synthesis for the Preparation of Quinoline Alkaloid Analogues

Abstract

A new one-step methodology has been introduced for the synthesis of quinoline alkaloid analogues. The reaction is based on a modification of the Mukaiyama aldol condensation, making use of the high reactivity of lactones or anhrydrides. The reaction is general and allows for the construction of new hetero polycondenced molecules in a one-step synthesis.

A Facile and Divergent Synthesis of Substituted Pyridine-2,4(1H,3H)-diones and 4H-Thiopyran-4-ones from α-Alkenoyl-α-carbamoyl Ketene-S,S-acetals

“…Actually, substituted pyridine-2,4(1H,3H)-diones and their benzofused derivatives represent an important class of aza-heterocycles that are widely distributed among a large number of alkaloids with useful biological and pharmacological activities. [14,15] Recently, Chen and coworkers reported the synthesis of 2(1H)-pyridinones via the Vilsmeier reaction of α-acyl-α-carbamoyl ketene-S,S-acetals 1. [16] In the present work, we provide a facile and efficient synthesis of substituted pyridine-2,4(1H,3H)-diones 3 from readily available α-acyl-α-carbamoyl ketene-S,S-acetals 1.…”

Six‐Membered Heterocycles: Quinoline and Isoquinoline

“…The reaction is based on a modification of the Mukaiyama aldol condensation and makes use of the high reactivity of benzoxazin-4-ones 90 in the presence of ketene silyl acetals 91 (Scheme 17.64) [146]. Substituted 2,4-quinolines can be obtained by a novel synthesis that involves cyclization and thermal extrusion of sulfur.…”

Untitled

“…The derivatives of quinoline have been synthesized by many routes in the search of potent therapeutic agents. Quinoline has a molecular formula C 9 H 7 N and molecular weight of 129.16 1 . Quinoline was first extracted from coal tar in 1934 by Friedel Ferdinand Runge.…”