Herein, we report a facile synthesis of 3,4-dihydro-β-carbolines and aromatic β-carbolines from tetrahydro-β-carbolines, mediated by N-bromosuccinimide in toluene at 0°C to room temperature (rt), in good to moderate yields. © 2016 Elsevier Ltd. All rights reserved.

Subhabrata Sen

Chemistry

(SoNS) School of Natural Sciences

Hati S.

<p>Shiv Nadar University is a comprehensive, multidisciplinary, research-focused, and student-centric University offering a full range of academic programs at the undergraduate, postgraduate and doctoral level. With state-of-the-art infrastructure, the University comprises of academic wings, sophisticated labs, international standard sports facilities, amphitheaters, auditorium, conference rooms and smart classrooms. The University&rsquo;s goal is to become internationally recognized for the quality of its research and creative endeavors and their applicability to improving quality of life, generating new insights and expanding the boundaries of human knowledge creativity. Committed to excellence in teaching, research and service, the University aims to serve the higher education needs of India and the world beyond.</p>

Shiv Nadar University

Tetrahedron Letters

Catalytic cerium chloride was found to activate 2-iodoxybenzoic acid (IBX) for the oxidative dehydrogenation of tetrahydroisoquinolines, tetrahydro-β-carbolines, and thiazolidines to their dehydrogenated and aromatic forms at room temperature in moderate to excellent yields. The robustness of the protocol was demonstrated by scaling up the reactions to multigram quantities. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

European Journal of Organic Chemistry

Cerium Chloride Catalyzed, 2-Iodoxybenzoic Acid Mediated Oxidative Dehydrogenation of Multiple Heterocycles at Room Temperature

Nitrogen heteroarenes form an important class of compounds which can be found in natural products, synthetic drugs, building blocks etc. Among the diverse strategies that were developed for the synthesis of nitrogen heterocycles, oxidative dehydrogenation is extremely effective. This review discusses various oxidative dehydrogenation strategies of C-C and C-N bonds to generate nitrogen heteroarenes from their corresponding heterocyclic substrates. The strategies are categorized under stoichiometric and catalytic usage of reagents that facilitate such transformations. The application of these strategies in the synthesis of nitrogen heteroarene natural products and synthetic drug intermediates are also discussed. We hope this review will arouse sufficient interest among the scientific community to further advance the application of oxidative dehydrogenation in the synthesis of nitrogen heteroarenes. © 2017 Hati et al.; Licensee Beilstein-Institut.

Fulltext

Beilstein Journal of Organic Chemistry

Oxidative dehydrogenation of C-C and C-N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

We have demonstrated a facile synthesis of diversely substituted quinazolines and 3,4-dihydroquinazolines through the o-iodoxybenzoic acid (IBX) mediated tandem reaction of readily available o-aminobenzylamine and aldehydes. The yield of the reactions generally ranged from 70\% to 95\%. This mild protocol provides an efficient strategy toward the synthesis of these classes of heterocycles. © Georg Thieme Verlag Stuttgart.

Synthesis (Germany)

Synthesis of Quinazolines and Dihydroquinazolines: o-Iodoxybenzoic Acid Mediated Tandem Reaction of o-Aminobenzylamine with Aldehydes

Organic & Biomolecular Chemistry

PhI(OAc)2-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: synthesis of norharmane, harmane, eudistomin U and eudistomin I

Journal of the American Chemical Society

Bioinspired Aerobic Oxidation of Secondary Amines and Nitrogen Heterocycles with a Bifunctional Quinone Catalyst

Journal of Photochemistry and Photobiology B: Biology

Binding of alkaloid harmalol to DNA: Photophysical and calorimetric approach

European Journal of Medicinal Chemistry

Synthesis and structure–activity relationships of N2-alkylated quaternary β-carbolines as novel antitumor agents

Synthetic Communications

Mild and Efficient Syntheses of 1-Aryl-3,4-dihydroisoquinolines and 1-Aryl-3,4-dihydro-β-carbolines via Regiospecific β-Eliminations of the CorrespondingN-Tosyl-1,2,3,4-tetrahydroisoquinolines andN-Tosyl-1,2,3,4-tetrahydro-β-carbolines

N-Bromo-succinimide promoted synthesis of β-carbolines and 3,4-dihydro-β-carbolines from tetrahydro-β-carbolines