130627-09-7Relevant articles and documents
Structural analogues of quinoline alkaloids: Straightforward route to [1,3]dioxolo[4,5-c]quinolines with antibacterial properties
?am?ulová, Veronika,Funk, Petr,Grepl, Martin,Horák, Radim,Hradil, Pavel,Ko?istek, Kamil,Kvapil, Lubomír,Slaninová, Ludmila,Soural, Miroslav
, (2020)
Compounds bearing [1,3]dioxolo-quinoline scaffolds have been found in quinoline-based natural products; the only exception is the [1,3]dioxolo[4,5-c]quinoline moiety with a rare occurrence in both natural and synthetic derivatives. In this article, we report the preparation of diversely substituted and functionalized [1,3]dioxolo[4,5-c]quinolines using [1,3]dioxolo[4,5-c]quinoline-4-carbaldehyde (DQC) as the common intermediate. DQC was synthesized on a large scale from anthranilic acid and chloroacetone as the starting materials, with the rearrangement of acetonyl-anthranilate as the key step. The developed method allows for the simple preparation of [1,3]dioxolo[4,5-c]quinolines with various C2 substituents on the quinoline scaffold. Additionally, the synthetic route was successfully applied to the preparation of 3-hydroxyquinoline-4(1H)-ones. The target compounds were tested against representative Gram-positive/negative bacteria, and two derivatives exhibited submicromolar minimum inhibitory concentrations against Micrococcus luteus.
Synthesis of 2-Substituted 1H-Benzoxazepin-5-ones
Sicker, Dieter
, p. 336 - 344 (2007/10/02)
An approach to the hitherto unknown class of 1H-benz>e>oxazepin-5-ones is given based on reduction and cyclization of appropriate acyclic ortho-nitro compounds as starting material.Thus, some 2-substituted derivatives (3a-i) were synthesized by catal
