Unexpected regiospecific Michael addition product: synthesis of 5,6-dihydrobenzo[1,7]phenanthrolines

Abstract

COMMUNICATION This journal isThe unexpected formation of 5,6-dihydrobenzo[1,7]phenanthroline instead of 5,6-dihydrobenzo[1,7]phenanthroline-3-carbonitrile has been observed in acridine molecules for the first time using Michael addition methodology. Moreover, we have identified Montmorillonite KSF clay as catalyst to offer regiospecific expected dihydrobenzo[1,7]phenanthroline-3-carbonitrile product and NaH base as regiospecific formation of unexpected Michael addition 5,6-dihydrobenzo[1,7]phenanthroline products. On the basis of systematic study, the novel regiospecificity could be assigned by utilization of suitable catalyst.

A Metal-Free Regioselective Multicomponent Approach for the Synthesis of Free Radical Scavenging Pyrimido-Fused Indazoles and Their Fluorescence Studies

“…The products display features of all the inputs and thus afford greater possibilities for molecular diversity [3]. The cascade/domino/tandem process [4,5,6], involves subsequent transformations of functionalities produced in the previous step [7]. Normally, these reactions are easier to carry out by one pot synthesis than multi-step synthesis [8].…”

Catalytic application of non-toxic Persia americana metabolite entrapped SnO2nanoparticles towards the synthesis of 3,4-dihydroacridin-1(2H)-ones

“…[12][13][14] But these methods lead to toxic effects to the environment and human health due to the usage of toxic solvents and chemicals. [15][16][17] Various biological heterocycles have been reported with chemical methods but they may be toxic. 18 To overcome these toxicity effects we have focused our research towards the environmentally friendly synthesis of SnO 2 NPs using Persia americana seed methanolic extract; furthermore, we have employed these for organic synthesis, i.e.…”

Regioselective access to di- and trisubstituted pyridines via a metal-oxidant-solvent-free domino reaction involving 3-chloropropiophenones

“…To demonstrate the synthetic utility of the prepared pyridines, the fused pyridine 4aaz was reacted with 2-aminoacetophenone using 20 mol% pTSA in toluene at 110 °C for 30 h. Pleasantly, an interesting class 28 of 5,6-dihydrobenzo[ b ][1,7]phenanthroline building block 14 was obtained in a 61% yield as shown in Scheme 8.…”