Synthesis, X-ray characterization and theoretical study of 3a,6:7,9a-diepoxybenzo[de]isoquinoline derivatives: on the importance of F⋯O interactions

Abstract

The synthesis, X-ray characterization and Hirshfeld surface analysis of a series of tetrahydro-diepoxybenzo[de]isoquinoline derivatives obtained by the tandem [4+2] cycloaddition between perfluorobut-2-yne dienophile (F3C–C≡C–CF3) and a row of N,N-bis(furan-2-ylmethyl)-4-R-benzenesulfonamides (bis-dienes,...

Crystal structure and Hirshfeld surface analysis of 2,2,2-trichloro-N,N-bis{[(1RS,4SR)-1,4-dihydro-1,4-epoxynaphthalen-1-yl]methyl}acetamide

“…Cascade sequences comprising two or more successive [4 + 2] cycloaddition steps are a powerful and frequently used protocol in modern syntheses aimed at constructing cyclohexene derivatives thanks to their exceptional chemoselectivity, regioselectivity, diastereoselectivity, and capability to create more than four chiral centers in a single synthetic step (Criado et al, 2010(Criado et al, , 2013. It has been shown previously that the Diels-Alder reaction of bis-dienes with derivatives of maleic acid, esters of acetylene dicarboxylic acid and hexa-fluoro-2-butyne proceeds in all cases diastereo-and chemoselectively and leads, depending on the temperature, to annelated diepoxynaphthalenes of the 'domino' or 'pincer' type (Borisova et al, 2018a,b;Grudova et al, 2020;Kvyatkovskaya et al, 2020Kvyatkovskaya et al, , 2021. In order to expand the limits of the applicability of the IMDAF strategy, we tested in this study dehydrobenzene generated in situ in the role of dienophile.…”

Crystal engineering of molecules with through-space α-effect hydrogen bonds: 3a,6 : 7,9a-diepoxybenzo[de]isoquinolines possessing a free amino group

“…In the last five years our research group has studied [1][2][3] the best conditions to achieve kinetic and thermodynamic control in tandem [4 + 2]/[4 + 2] cycloaddition reactions, using activated alkynes/alkenes and bis-dienes. During these investigations, an extensive family of hydrogenated or partially hydrogenated naphthalenes, bearing from two to four epoxy bridges, has been generated and their physiochemical properties studied.…”

Role of Halogen Substituents on Halogen Bonding in 4,5-DiBromohexahydro-3a,6-Epoxyisoindol-1(4H)-ones

“…On the other hand, the isoindole synthon is an important structural unit in many natural products and bioactive compounds, as well as a useful building-block for the construction of new N-containing heterocyclic compounds [27][28][29][30][31][32][33][34]. For instance, heterocyclic compounds containing isoindole moieties have demonstrated a promising biological action and pharmacological activity as pathogen antagonists [29].…”

“…For instance, heterocyclic compounds containing isoindole moieties have demonstrated a promising biological action and pharmacological activity as pathogen antagonists [29]. The isoindole motif can also be involved as a versatile and powerful intermediate for the synthesis of various chiral heterocyclic compounds with unique properties [27][28][29][30][31][32][33][34]. Thus, the functionalization of isoindole moieties with noncovalent bond donor/acceptor sites can improve their photophysical properties [27], bioactivity [32], coordination ability [35,36], etc.…”