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Pericyclic Reactions

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 July 2016) | Viewed by 45939

Special Issue Editor

School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, VIC 3010, Australia
Interests: total synthesis; natural products; methods development; asymmetric synthesis; myxobacteria metabolites; pericyclic reactions

Special Issue Information

Dear Colleagues,

Pericyclic reactions are seminal processes in organic synthesis. They have long been utilised to form multiple bonds and stereocenters in a single operation, and have found application in the total synthesis of natural products and a multitude of other endeavours. This Special Issue will feature contributions from renowned international researchers in organic synthesis in which pericyclic reactions feature as key transformations.

Prof. Dr. Mark A. Rizzacasa
Guest Editor

Manuscript Submission Information

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Keywords

  • pericyclic
  • rearrangements
  • cycloadditions
  • stereoselective
  • total synthesis

Published Papers (6 papers)

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Research

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1465 KiB  
Article
Efficient Synthesis of Fully Substituted Pyrrolidine-Fused 3-Spirooxindoles via 1,3-Dipolar Cycloaddition of Aziridine and 3-Ylideneoxindole
by Wen Ren, Qian Zhao, Chuan Zheng, Qiong Zhao, Li Guo and Wei Huang
Molecules 2016, 21(9), 1113; https://doi.org/10.3390/molecules21091113 - 24 Aug 2016
Cited by 5 | Viewed by 7136
Abstract
Drug-like spirocyclic scaffolds have been prepared by fusing fully functionalized pyrrolidine with oxindoles in an approach based on 1,3-dipolar cycloaddition. Reaction between aziridine and 3-ylideneoxindole generated diverse spirooxindole-pyrrolidines in good yield (up to 95%) with high diastereoselectivity (up to >20:1). The reaction also [...] Read more.
Drug-like spirocyclic scaffolds have been prepared by fusing fully functionalized pyrrolidine with oxindoles in an approach based on 1,3-dipolar cycloaddition. Reaction between aziridine and 3-ylideneoxindole generated diverse spirooxindole-pyrrolidines in good yield (up to 95%) with high diastereoselectivity (up to >20:1). The reaction also proceeded smoothly with several other synthetically useful activated trisubstituted olefins. The mild reaction conditions, short reaction times, and high tolerance for various substitutions make this approach attractive for constructing pharmacologically interesting spiro-architectures. Full article
(This article belongs to the Special Issue Pericyclic Reactions)
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4434 KiB  
Article
Ultrasonic Synthesis, Molecular Structure and Mechanistic Study of 1,3-Dipolar Cycloaddition Reaction of 1-Alkynylpyridinium-3-olate and Acetylene Derivatives
by Asmaa Aboelnaga, Mohamed Hagar and Saied M. Soliman
Molecules 2016, 21(7), 848; https://doi.org/10.3390/molecules21070848 - 29 Jun 2016
Cited by 28 | Viewed by 5168
Abstract
Regioselectively, ethyl propiolate reacted with 1-(propergyl)-pyridinium-3-olate to give two regioisomers; ethyl 4-oxo-8-(prop-2-ynyl)-8-aza-bicyclo(3.2.1)octa-2,6-diene-6-carboxylate 4, ethyl 2-oxo-8-(prop-2-ynyl)-8-aza-bicyclo(3.2.1)octa-3,6-diene-6-carboxylate 5 as well as ethyl 2,6-dihydro-6-(prop-2-ynyl)furo(2,3-c)pyridine-3-carboxylate 6. The obtained compounds were identified by their spectral (IR, mass and NMR) data. Moreover, DFT quantum chemical calculations were [...] Read more.
Regioselectively, ethyl propiolate reacted with 1-(propergyl)-pyridinium-3-olate to give two regioisomers; ethyl 4-oxo-8-(prop-2-ynyl)-8-aza-bicyclo(3.2.1)octa-2,6-diene-6-carboxylate 4, ethyl 2-oxo-8-(prop-2-ynyl)-8-aza-bicyclo(3.2.1)octa-3,6-diene-6-carboxylate 5 as well as ethyl 2,6-dihydro-6-(prop-2-ynyl)furo(2,3-c)pyridine-3-carboxylate 6. The obtained compounds were identified by their spectral (IR, mass and NMR) data. Moreover, DFT quantum chemical calculations were used to study the mechanism of the cycloaddition reaction. The regioselectivity was explained using transition state calculations, where the calculations agreed with the formation of products 4 and 5 in almost the same ratio. The reaction was also extended for diphenylaceylene as dipolarophile to give only two products instead of three. Full article
(This article belongs to the Special Issue Pericyclic Reactions)
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2175 KiB  
Article
Rearrangements of Cycloalkenyl Aryl Ethers
by Mercedesz Törincsi, Melinda Nagy, Tamás Bihari, András Stirling, Pál Kolonits and Lajos Novak
Molecules 2016, 21(4), 503; https://doi.org/10.3390/molecules21040503 - 19 Apr 2016
Cited by 1 | Viewed by 5998
Abstract
Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-substituted phenol and naphthol derivatives. In the [...] Read more.
Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-substituted phenol and naphthol derivatives. In the case of cycloocthylphenyl ether the consecutive Claisen and Cope rearrangements were followed by an alkyl migration. The mechanism of this novel rearrangement reaction is also discussed. Full article
(This article belongs to the Special Issue Pericyclic Reactions)
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2242 KiB  
Article
1,3-Dipolar Cycloaddition in the Preparation of New Fused Heterocyclic Compounds via Thermal Initiation
by Martin Porubský, Lukáš Tenora and Milan Potáček
Molecules 2016, 21(2), 187; https://doi.org/10.3390/molecules21020187 - 04 Feb 2016
Cited by 3 | Viewed by 4733
Abstract
This paper describes the synthesis of precursors with a benzo[b]furan skeleton for the intramolecular 1,3-dipolar cycloaddition of azomethine ylides prepared from N-substituted 3-allyl-aminobenzo[b]furan-2-aldehydes and secondary amines derived from α-amino acid esters. Reactions were initiated by heating. The products [...] Read more.
This paper describes the synthesis of precursors with a benzo[b]furan skeleton for the intramolecular 1,3-dipolar cycloaddition of azomethine ylides prepared from N-substituted 3-allyl-aminobenzo[b]furan-2-aldehydes and secondary amines derived from α-amino acid esters. Reactions were initiated by heating. The products consisted of four fused rings with three stereogenic centers. Their structure and stereochemistry were determined by NMR spectra and X-ray measurements. Full article
(This article belongs to the Special Issue Pericyclic Reactions)
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2433 KiB  
Communication
DFT Studies on the Stereoselectivity of α-Silyloxy Diazoalkane Cycloadditions
by Matthew J. O’Connor, Huaqing Liu, Daesung Lee, Tao Zhou and Yuanzhi Xia
Molecules 2015, 20(12), 21433-21441; https://doi.org/10.3390/molecules201219783 - 02 Dec 2015
Viewed by 6296
Abstract
The intramolecular [3+2] cycloaddition (32CA) of alkene-tethered α-silyloxydiazoalkanes provides variable stereoselectivity in generating bicyclic pyrazolines where the silyloxy group is either syn or anti to the newly formed pyrazoline ring. To elucidate the origin of the stereoselectivity, density functional theory (DFT) calculations were [...] Read more.
The intramolecular [3+2] cycloaddition (32CA) of alkene-tethered α-silyloxydiazoalkanes provides variable stereoselectivity in generating bicyclic pyrazolines where the silyloxy group is either syn or anti to the newly formed pyrazoline ring. To elucidate the origin of the stereoselectivity, density functional theory (DFT) calculations were carried out for the energy of each transition state structure (TSs) and product. Steric effects were identified as the major determining factors in the diastereoselectivity of the 32CA reaction with regards to substrate structure (cyclic or acyclic α-silyloxydiazoalkanes). Full article
(This article belongs to the Special Issue Pericyclic Reactions)
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Review

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23154 KiB  
Review
1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives
by Adam G. Meyer and John H. Ryan
Molecules 2016, 21(8), 935; https://doi.org/10.3390/molecules21080935 - 23 Jul 2016
Cited by 72 | Viewed by 15507
Abstract
We provide a comprehensive account of the 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles. Many different azomethine ylides have been studied, including stabilized and non-stabilized ylides. Of the carbonyl dipolarophiles, aldehydes including formaldehyde are the most studied, although there are now [...] Read more.
We provide a comprehensive account of the 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles. Many different azomethine ylides have been studied, including stabilized and non-stabilized ylides. Of the carbonyl dipolarophiles, aldehydes including formaldehyde are the most studied, although there are now examples of cycloadditions with ketones, ketenes and carboxyl systems, in particular isatoic anhydrides and phthalic anhydrides. Intramolecular cycloadditions with esters can also occur under certain circumstances. The oxazolidine cycloadducts undergo a range of reactions triggered by the ring-opening of the oxazolidine ring system. Full article
(This article belongs to the Special Issue Pericyclic Reactions)
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