Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction

Abstract

A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic and kinetic study, some controlled experiments and deuterium labeling experiments were executed. A time-dependent product distribution experiment is also presented and the reaction scale-up is performed to highlight the practical utility of this strategy.

Water‐Promoted Metal‐Free Aerobic Oxidative Annulation for the Multicomponent Synthesis of Acridine‐1,8‐Diones Derivatives and Their Photophysical Studies

“…of TBHP were inferior to that achieved with 2 eq. (entries [11][12]. Surprisingly, the reaction failed to produce the expected product when the reaction was regulated under N 2 atmosphere which indicates that the reaction requires a strong oxidizing atmosphere for the product formation (entry 13).…”

“…[10] Recently, a couple of reports presented the synthesis of acridine-1,8-diones via benzyl alcohol using metal catalysts (Scheme 1b). [5,11,12] The utilization of expensive noble or transition metals, phosphine-based ligands, and the requirement for harsh reaction conditions has provided an opportunity for developing alternative synthetic procedures for large-scale applications under relatively moderate circumstances employing affordable metal-free reagents.…”

An Efficient Combinatorial Synthesis of Novel Thiazolidinone‐Bis Schiff Base Hybrids Using One‐Pot Multicomponent Reaction

“…13 C NMR (CDCl 3 , 125 MHz): δc (ppm) 170. 3,161.6,159.5,158.7 (dd,CF,J = 253.75 Hz, J = 3.75 Hz), 134.1,131.4 (t,CF,J = 8.5 Hz),131.0,128.8,128.3,112.4 (dd, CF, J = 18.75 Hz, J = 2.5 Hz), 32.30. HR-MS (ESI) for C 16 H 11 N 3 OF 2 S m/z [M + H] + calcd: 332.0661, found:332.0641.…”

“…[2] The MCRs also offer a fine-tuning of the reaction parameters to achieve the targeted molecule by suppressing the side product formation. [3] Due to these advantages, the development of novel and versatile MCRs targeting the synthons having multiple reactive sites, is highly exigent. [4] Hybrid molecule approach of drug design has recently attracted a great deal of attention due to the benefits such as delayed resistance, reduced toxicity, ease of treatment of coinfection, and lower cost of preclinical evaluation.…”

One Pot Three Component Synthesis of Substituted 3,4,6,7-Tetrahydro-3,3,6,6-Tetramethyl-9,10-Diphenylacridine-1,8(2H,5H,9H,10H)-Diones Catalyzed by Mesostrucrted In2O3-SiO2

“…Literature survey, the 1,8-dioxo-decahydroacridines syntheised by various researchers have been reported, in which 1,3-Di (bromo or chloro)-5,5-Dimethylhydantoin [23], Sulfonic acid functionlized silica (SiO 2 -Pr-SO 3 H) [24], nano-Fe 2 O 3 [25], HCl [26], Fe 3 O 4 @SiO 2 -MoO 3 H nanoparticles [27], Ru-catalyst [28], Ionic liquid with multi-SO 3 H groups [29] like this various catalyst were used for the synthesis but In 2 O 3 -SiO 2 combination of binary mixed metal oxide till this date not utilized for it.…”