(Chemical Equation Presented) The one-pot reaction of 2-tetralone with ammonium acetate and substituted benzaldehydes affords in a good yield of 5-aryl-7,8,13,14-tetrahydrodibenzo[a,i]phenanthridine or 2,4-diaryl-6,7-benzo-3- azabicyclo[3.3.1]nonan-9-one. The course of the reaction seems to be dictated by the position of the substituents present on the benzaldehyde ring. © 2009 HeteroCorporation.

Sathiyanarayanan K

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Shanthi S

Karthikeyan N.S

Aravindan P.G

Rathore R.S

Lee C.W.

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

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VIT University

Journal of Heterocyclic Chemistry

First of its kind inkjet-printed phosphorescent Iridium(III) complex [Ir(TPQ)2(4-EO2-pic)] paper based chemosensor has been developed for Hg2+ ions. The probe is highly selective towards mercury analyte over other metal ions (Cu2+, Ca2+, Co2+, Cd2+, Pb2+, Zn2+, Ni2+, Mg2+, Mn2+, Al3+, Fe3+, La3+, Ag+, K+, Na+ and Li+). [Ir(TPQ)2(4-EO2-pic)] complex solution gave a visible color change from orange to yellow and significant phosphorescence quenching. Upon addition of aqueous Hg2+, the [Ir(TPQ)2(4-EO2-pic)] inkjet-printed paper gave a significant color change in both normal and UV light. The detection limit was found out as 1.78 × 10−8 M. Cyclic voltammetry (CV) studies were conducted to explore the further utility of [Ir(TPQ)2(4-EO2-pic)] as electrochemical sensor for Hg2+ ions in CH3CN/H2O (v/v = 1/1). The oxidation wave intensity of [Ir(TPQ)2(4-EO2-pic)] at 0.98 V decreased and new reversible oxidation wave was appeared at 0.91 V The binding ratio of the [Ir(TPQ)2(4-EO2-pic)]-Hg2+ complex was determined to be 1:1 according to the Job's Plot. The probable binding modes of these [Ir(TPQ)2(4-EO2-pic)] with Hg2+ have also been suggested on the basis of the 1H NMR titration, absorption and luminescence studies. © 2018

Dyes and Pigments

Inkjet-printed phosphorescent Iridium(III) complex based paper sensor for highly selective detection of Hg2+

A new sulfur-bearing phenanthridine probes were synthesized and examined for their cation recognition abilities towards different cations in aqueous ACN solution and paper strips.

New Journal of Chemistry

Development of paper-based chemosensor for the detection of mercury ions using mono- and tetra-sulfur bearing phenanthridines

Highly luminescent, 5−aryl−7,8,13,14-tetrahydrodibenzo[a,i]phenanthridines (THDPs) in Donor(D)−π−Acceptor(A), A−π−A, A−π−A−π−A1 configurations were synthesized in good to moderate yields by simple, two step reactions. All the phenyl rings were found to be in near-coplanar configuration due to the enforced planarity by the ethylene bridge. As a result, efficient π-conjugation was maintained throught the molecule. UV–visible absorption and fluorescence spectra of THDP became shifted to longer wavelengths upon substitution of different moieties at 5-Aryl position. A maximum of 200 nm red-shifted fluorescence with respect to parent compound was observed for the nitro substituent. However, tradeoffs in spectral shifts were noticed when two strongly electron withdrawing groups such as nitro and cyano groups were present simultaneously. Presence of one or more acceptors induced the intramolecular electron transfer processes, and the photophysical properties of THDP core was tuned by different substituents. Application of this fluorophore has also been demonstrated by means of DNA interaction studies. © 2016 Elsevier Ltd

Photophysical studies of donor, acceptor substituted tetrahydrodibenzo[a,i]phenanthridines

A series of luminescent 5-aryl-tetrahydrodibenzo[a,i]phenanthridines was developed through modified synthetic protocol using SnCl2-acetic acid as a catalyst. The synthesis was consistent with various functionalities and significantly improves the yields. These derivatives exhibit large molar absorption coefficients and higher Stokes shift values in the range 9739-2628 cm-1. The donor and acceptor groups significantly induced the charge transfer character leading to widespread emission properties in the range of 390-531 nm with moderate quantum yields. The protonation and quaternization studies of these derivatives revealed the formation of a new red shifted absorption band followed by hyperchromic effect in emission, which could be used as an acidochromic sensor. © 2016 Elsevier Ltd. All rights reserved.

Synthesis, photophysical and acidochromic properties of a series of tetrahydrodibenzo[a,i]phenanthridine chromophores

The diastereoselective direct one-pot three-components Mannich reaction of cyclododecanone (CDD), which has a unique conformation with aromatic aldehydes and anilines in the presence of catalytic amount of ammonium acetate was studied. The catalyzed reaction offered high yield, high diastereoselectivity, and simple workup. The addition of aniline to the aldol product took place, and this addition was made to the less hindered α-side. The Mannich derivatives were found to exhibit anti-cancer activities against six human cancer cell lines. This was observed using the CCK-8 nonradioactive colorimetric assay and the results were compared with MCFA10 normal breast epithelium cell line. A significant difference was observed in anti-cancer activity of anti (7f-7h) and syn (7ff-7hh) isomers in human cancer cell lines. Graphical abstract: The diastereoselective direct one-pot three-components, Mannich reaction of CDD, having unique conformation, with aromatic aldehydes and anilines in the presence of catalytic amount of NH4OAc giving anti/syn products was studied. The β-amino-carbonyl compounds are potent human anti-cancer cell lines and analogues of 7h-g anti-isomers are active in anti-cancer cell line whereas 7hh-gg syn-isomer is inactive.[Figure not available: see fulltext.] © 2014 Springer Science+Business Media New York.

Medicinal Chemistry Research

A mild and efficient one-pot three-component synthesis of anti-β-amino-carbonyl compounds catalyzed by NH4OAc and their anticancer activities

Tetrahedron Letters

A new synthesis of the benzo[c]phenanthridines nornitidine, noravicine, and isodecarine, based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system

Bioorganic & Medicinal Chemistry

11-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine derivatives as novel topoisomerase I-targeting agents

Syntheses of phenanthridines and benzophenanthridines by intramolecular ortho-arylation of aryl amide ions with aryl halides via SRN1 reactions

Tetrahedron

The reaction of tetralones with nitriles: a simple approach to the synthesis of new substituted benzo[h]quinazolines, benzo[f]quinazolines and dibenzo[a,i]phenanthridines

A novel aromatic alkylation of anilines with cyclic and acyclic ketones under hydrothermal conditions

Dual behavior of 2-tetralone: A new approach for the synthesis of 5-aryl-7,8,13,14-tetrahydrodibenzo[a,i]phenanthridine

Journal	Data powered by TypesetJournal of Heterocyclic Chemistry
Publisher	Data powered by TypesetWiley
ISSN	0022-152X
Open Access	0