Potential antidepressants and tranquillizers: Synthesis of some 9-(aminoalkoxy)-2,3,6,7-tetrahydro-1H,5H-benzo[ij] quinolizines and 1-(substituted amino)-3-(1-naphthoxy)-2-propanols

Abstract

The hydrobromide of 9-hydroxyjulolidine was reacted with hydrochloride of 2-dimethylaminoethyl chloride, 2-(I-pyrrolidinyl)ethyl chloride, 2-(I-piperidinyl)ethyl chloride, and 3-dimethylaminopropyl chloride in ethanol in the presence of sodium ethoxide to give the title bases 11-V which were transformed to dihydrochlorides. Heating of 1,2-epoxy-3-(I-naphthoxy)propane with 2,3, 3-trimethy 1-2-buty lamine, I-me thy Icyclopenty lamine, I-me thy Icyclohexy lamine, 1--methylcycloheptylamine, and 1O,II-dihydrodibenzo[a, d]cycloheptene-5-amine in ethanol afforded the second part of the title compounds (VII-Xl), prepared also in the form of hydrochi rides. Only the ethers 11 and V showed indications of possible antidepressant activity.

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

“…Heteropolycycles based on julolidine are extremely valuable and are applied in industry and also in biological systems, such as photoconductive materials,25 nonlinear optical materials,26,27 highly fluorescent molecular rotors,28,29 chemiluminescent dyes,30,31 chromogenic substrates in analytical redox reactions,32 potential antidepressants and tranquilizers 33. Considering the importance of the julolidine structural motif, the synthesis of new structurally diverse julolidine derivatives that can benefit from its properties represents a challenge27,34,35 and, recently, the first synthesis of a julolidine‐fused heteroaromatic with coumarin has been reported for application as a fluorescent label 36…”

Catalytic Asymmetric Aza‐Diels‐Alder Reaction: Pivotal Milestones and Recent Applications to Synthesis of Nitrogen‐Containing Heterocycles

“…Immediate stereoselective reduction of rather unstable unsaturated amination product 216 with sodium triacetoxyborohydride and acetic acid afforded julolidine analogs 217 with up to 99:1 dr and 99% ee . Julolidine and its derivatives are considered as potential antidepressants/tranquilizers [228] and chemiluminescence materials [229] …”

Microwave-assisted multicomponent synthesis of julolidines using silica-supported calix[4]arene as heterogeneous catalyst

“…28 2.6. 13 C and 29 Si MAS-NMR 13 C MAS-NMR of pure CX4SO 3 H (Figure 3a) present the following peaks: 30.1 (-CH2-); 127.9 (Ar); 137.0 (Ar); 150.6 (Ar). These signals are also present in the CX4SO 3 HSi(n) (Figure 3b), which proves that the CX4SO 3 H structure is maintained after the inclusion.…”

“…8 On the other hand, the application of calix [n]arenes as a heterogeneous catalyst for the chemical transformations remains largely unexplored. 2e ,9 Julolidine and their derivatives are one of the most versatile and important classes of N-heterocyclic and have attracted enormous attention from the scientific community for the potential in many applications such as for metal sensing, 10 dyesensitized solar cells, 11 antiviral activity, 12 antidepressants, 13 tranquilizers, 14 fluorescent probe, 15 and nonlinear optical materials 16 (Figure 1). Figure 1.…”