Structural comparison of five new halogenated dihydroquinoline-4(1H)-ones

Abstract

Compounds with dihydroquinoline-4(1H)-one nuclei have been reported in the literature for being important in the development of medicines due to their broad spectrum of activities. In this way, the structural knowledge of this class becomes relevant for obtaining new materials with desired biological properties. This study presents the structural elucidation of five halogenated dihydroquinolines, as well as the discussion about the effect on the molecular conformation of the type and position of halogen atom on aromatic rings. Compounds I and IV differ in halogen substitution on 2-phenyl ring, while compounds III and V differ in halogen substitution on the benzylidene ring. Moreover, compound II has a para-substituted 2-phenyl ring in their molecular structure. The crystal packing of all five molecules is mainly ruled by CeH/O and CeH$$$halogen interactions that form dimers and chains. The shift in position and the kind of the halogen in ring C shows a starring role in the conformation of the studied compounds, and the packaging of these compounds is more susceptible to variations when the halogen position changes.

Synthesis, Structural and Biological Properties of the Ring-A Sulfonamido Substituted Chalcones: A Review

“…The presence of the ambident electrophilic α,βunsaturated carbonyl framework and its proximity to the nucleophilic ortho-sulfonamido group have long been exploited as templates for the base-mediated cyclization to afford the 2-aryl-1-(alkyl/arylsufonyl)-2,3-dihydroquinolin-4(1H)-ones [27][28][29] with increased propensity to undergo regio-and stereoselective C-3 halogenation [30]. Base-mediated cyclization-condensation with benzaldehyde derivatives, on the other hand, afforded the 2-aryl-1-(arylsulfonyl)-3-benzylidene-2,3-dihydroquinolin-4(1H)-ones [31,32].…”