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Advances in Heteroaromatic Chemistry
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Advances in Heteroaromatic Chemistry

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 December 2012) | Viewed by 94378

Special Issue Editor

Dr. Guy L. Plourde

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Guest Editor
Department of Chemistry, University of Northern British Columbia, 3333 University Way, Prince George, BC V2N 4Z9, Canada
Interests: spiroannulation; asymmetric methods; spirocompounds; natural products; manumycins
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Aromatic heterocyclic chemistry is a vast subject that has been and continues to be a focus of interest in both the academic and industrial worlds. Aromatic heterocycles are found in nature (for example in nucleic acids and indole alkaloids) and have been widely used as herbicides, fungicides, insecticides, dyes, and as pharmaceuticals.

The cyclic structure of these compounds must contain at least one heteroatom (usually N, O or S) and may vary in size (5 and 6-membered heterocyclic structures are most common). The aromaticity of these compounds can be viewed in two different ways: (a) it is inherited (for example aniline) because the structure meets all the standard conditions associated with aromaticity, or (b) it is earned (for example pyrrole) via the delocalization of a lone pair of electrons from the heteroatom.

This special issue of Molecules will consider any submissions associated with heteroaromatic chemistry (including but not limited to: biological, theoretical and mechanistic studies). However, the primary focus of this special issue is related to the synthesis and reactions of heteroaromatic compounds.

Dr. Guy L. Plourde
Guest Editor

Related Special Issues

Keywords

  • synthesis and reactions of heteroaromatic compounds
  • natural products
  • hetereocycles
  • bioassay
  • pharmaceutical

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Published Papers (7 papers)

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Research

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14 pages, 324 KiB  
Article
Palladium-Catalyzed Amination of Dichloroquinolines with Adamantane-Containing Amines
by Anton S. Abel, Alexei D. Averin, Olga A. Maloshitskaya, Evgenii N. Savelyev, Boris S. Orlinson, Ivan A. Novakov and Irina P. Beletskaya
Molecules 2013, 18(2), 2096-2109; https://doi.org/10.3390/molecules18022096 - 6 Feb 2013
Cited by 10 | Viewed by 5846
Abstract
Pd-catalyzed amination of isomeric 2,6-, 2,8-, 4,8- and 4,7-dichloroquinolines was studied using adamantane-containing amines in which substituents at the nitrogen atom differ in bulkiness. The selectivity of the amination of 2,6-dichloroquinoline was very low, substantially better results were obtained with 2,8-dichloroquinoline, and 4,8- [...] Read more.
Pd-catalyzed amination of isomeric 2,6-, 2,8-, 4,8- and 4,7-dichloroquinolines was studied using adamantane-containing amines in which substituents at the nitrogen atom differ in bulkiness. The selectivity of the amination of 2,6-dichloroquinoline was very low, substantially better results were obtained with 2,8-dichloroquinoline, and 4,8- and 4,7-dichloroquinolines provided the best yields of the amination products. Diamination of 4,8- and 4,7-dichloroquinolines was carried out with two amines which differ strongly in the bulkiness of the alkyl group. In the majority of cases BINAP ligand was successfully applied, however, it had to be replaced with DavePhos in certain reactions when using the most sterically hindered amine as well as for the diamination reactions. Full article
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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10 pages, 416 KiB  
Communication
Highly Efficient and Reusable Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides
by A Young Kim, Hyun Ju Lee, Ji Chan Park, Hyunju Kang, Haesik Yang, Hyunjoon Song and Kang Hyun Park
Molecules 2009, 14(12), 5169-5178; https://doi.org/10.3390/molecules14125169 - 10 Dec 2009
Cited by 58 | Viewed by 12264
Abstract
CuO/AB was found to be a simple and efficient catalyst for the N-arylation of a variety of nitrogen-containing heterocycles, giving the products in excellent yields. Full article
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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10 pages, 239 KiB  
Article
3-(2-Aminophenyl)-4-methyl-1,3-thiazole-2(3H)-thione as an Ecofriendly Sulphur Transfer Agent to Prepare Alkanethiols in High Yield and High Purity
by Mohammed Amine Mehdid, Ayada Djafri, Christian Roussel and Federico Andreoli
Molecules 2009, 14(11), 4634-4643; https://doi.org/10.3390/molecules14114634 - 12 Nov 2009
Cited by 5 | Viewed by 12347
Abstract
A new process is described for preparing very pure linear alkanethiols and linear α,ω-alkanedithiols using a sequential alkylation of the title compound, followed by a ring closure to quantitatively give the corresponding 3-methyl[1,3]thiazolo[3,2-a]-[3,1]benzimidazol-9-ium salt and the alkanethiol derivative under mild conditions. The alkanethiol [...] Read more.
A new process is described for preparing very pure linear alkanethiols and linear α,ω-alkanedithiols using a sequential alkylation of the title compound, followed by a ring closure to quantitatively give the corresponding 3-methyl[1,3]thiazolo[3,2-a]-[3,1]benzimidazol-9-ium salt and the alkanethiol derivative under mild conditions. The alkanethiol and the heteroaromatic salt are easily separated by a simple extraction process. The intermediate thiazolium quaternary salts resulting from the first reaction step can be isolated in quantitative yields, affording an odourless protected form of the thiols. Full article
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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12 pages, 239 KiB  
Article
An Efficient Method for the N-Bromosuccinimide Catalyzed Synthesis of Indolyl-Nitroalkanes
by Chun-Wei Kuo, Chun-Chao Wang, Hu-Lin Fang, B. Rama Raju, Veerababurao Kavala, Pateliya Mujjamil Habib and Ching-Fa Yao
Molecules 2009, 14(10), 3952-3963; https://doi.org/10.3390/molecules14103952 - 9 Oct 2009
Cited by 24 | Viewed by 12375
Abstract
An efficient and practical method for the synthesis of indolyl-nitroalkane derivatives catalyzed by N-bromosuccinimide is described. The generality of this method was demonstrated by synthesizing an array of diverse 3-substituted indole derivatives by the reaction of different β-nitrostyrenes with various substituted indoles. [...] Read more.
An efficient and practical method for the synthesis of indolyl-nitroalkane derivatives catalyzed by N-bromosuccinimide is described. The generality of this method was demonstrated by synthesizing an array of diverse 3-substituted indole derivatives by the reaction of different β-nitrostyrenes with various substituted indoles. Simple reaction conditions accompanied by good yields of indolyl-nitroalkanes are the merits of this methodology. Full article
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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11 pages, 308 KiB  
Article
Wet Aerobic Oxidation of Lignin into Aromatic Aldehydes Catalysed by a Perovskite-type Oxide: LaFe1-xCuxO3 (x=0, 0.1, 0.2)
by Junhua Zhang, Haibo Deng and Lu Lin
Molecules 2009, 14(8), 2747-2757; https://doi.org/10.3390/molecules14082747 - 27 Jul 2009
Cited by 101 | Viewed by 14645
Abstract
The perovskite-type oxide catalyst LaFe1-xCuxO3 (x=0, 0.1, 0.2) was prepared by the sol–gel method, and tested as a catalyst in the wet aerobic oxidation (WAO) of lignin into aromatic aldehydes. The lignin conversion and the yield of each [...] Read more.
The perovskite-type oxide catalyst LaFe1-xCuxO3 (x=0, 0.1, 0.2) was prepared by the sol–gel method, and tested as a catalyst in the wet aerobic oxidation (WAO) of lignin into aromatic aldehydes. The lignin conversion and the yield of each aromatic aldehyde were significantly enhanced in the catalytic process, compared with the non-catalyzed process. Moreover, it was shown that the stability of activity and structure of LaFe1-xCuxO3 (x=0, 0.1, 0.2) remained nearly unchanged after a series of successive recyclings of the catalytic reactions, indicating it was an efficient and recyclable heterogeneous catalyst for the conversion of lignin into aromatic aldehydes in the WAO process. Full article
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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Review

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22 pages, 940 KiB  
Review
Modifications on the Basic Skeletons of Vinblastine and Vincristine
by Péter Keglevich, László Hazai, György Kalaus and Csaba Szántay
Molecules 2012, 17(5), 5893-5914; https://doi.org/10.3390/molecules17055893 - 18 May 2012
Cited by 94 | Viewed by 20067
Abstract
The synthetic investigation of biologically active natural compounds serves two main purposes: (i) the total synthesis of alkaloids and their analogues; (ii) modification of the structures for producing more selective, more effective, or less toxic derivatives. In the chemistry [...] Read more.
The synthetic investigation of biologically active natural compounds serves two main purposes: (i) the total synthesis of alkaloids and their analogues; (ii) modification of the structures for producing more selective, more effective, or less toxic derivatives. In the chemistry of dimeric Vinca alkaloids enormous efforts have been directed towards synthesizing new derivatives of the antitumor agents vinblastine and vincristine so as to obtain novel compounds with improved therapeutic properties. Full article
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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21 pages, 532 KiB  
Review
Synthesis of Heteroaromatic Compounds by Oxidative Aromatization Using an Activated Carbon/Molecular Oxygen System
by Yuka Kawashita and Masahiko Hayashi
Molecules 2009, 14(8), 3073-3093; https://doi.org/10.3390/molecules14083073 - 14 Aug 2009
Cited by 40 | Viewed by 15805
Abstract
A variety of heteroaromatic compounds, such as substituted pyridines, pyrazoles, indoles, 2-substituted imidazoles, 2-substituted imidazoles, 2-arylbenzazoles and pyrimidin-2(1H)-ones are synthesized by oxidative aromatization using the activated carbon and molecular oxygen system. Mechanistic study focused on the role of activated carbon in [...] Read more.
A variety of heteroaromatic compounds, such as substituted pyridines, pyrazoles, indoles, 2-substituted imidazoles, 2-substituted imidazoles, 2-arylbenzazoles and pyrimidin-2(1H)-ones are synthesized by oxidative aromatization using the activated carbon and molecular oxygen system. Mechanistic study focused on the role of activated carbon in the synthesis of 2-arylbenzazoles is also discussed. In the final section, we will disclose the efficient synthesis of substituted 9,10-anthracenes via oxidative aromatization. Full article
(This article belongs to the Special Issue Advances in Heteroaromatic Chemistry)
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