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Domino Reactions
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Domino Reactions

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

Deadline for manuscript submissions: closed (20 January 2014) | Viewed by 27356

Special Issue Editor

Prof. Dr. Frederick G. West

E-Mail Website
Guest Editor
Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB T6G 2G2, Canada
Interests: novel strategies for the efficient construction of complex natural products; new methodology based on unusual reactive intermediates; de novo design of bioactive small molecules for use in imaging and therapeutics

Special Issue Information

Dear Colleagues,

This Special Issue of Molecules "Domino Reactions" is devoted to outstanding research and review papers focused on new synthetic methodology employing domino or cascade processes. The central concept should entail a sequence of consecutive reactions resulting in the formation of several new bonds. It may include, but is not limited to, processes involving catalytic methods, photochemical activation, multicomponent reactions, or enantioselectivity. Research papers and reviews describing new examples of such reactions or their application in target-directed synthesis are welcome for this Special Issue of Molecules. We ask that authors contemplating submission of review papers make a pre-submission inquiry to the guest editor with a brief outline of the proposed coverage.

Prof. Dr. Frederick G. West
Guest Editor

Submission

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed Open Access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs).


Keywords

  • domino reaction
  • cascade process
  • multicomponent reaction
  • transition metal catalysis
  • organocatalysis
  • carbocations
  • carbanions
  • radical reactions
  • metallocarbenes

Published Papers (3 papers)

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Research

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420 KiB  
Article
Easy Access to a Cyclic Key Intermediate for the Synthesis of Trisporic Acids and Related Compounds
by José A. González-Delgado, Gustavo Escobar, Jesús F. Arteaga and Alejandro F. Barrero
Molecules 2014, 19(2), 1748-1762; https://doi.org/10.3390/molecules19021748 - 03 Feb 2014
Cited by 3 | Viewed by 7481
Abstract
The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a D1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a [...] Read more.
The synthesis of a cyclohexane skeleton possessing different oxygenated functional groups at C–3, C–8 and C–9, and a D1,6-double bond has been accomplished in 10 steps with an overall 17% yield. This compound is a key intermediate for access to a wide range of compounds of the bioactive trisporoid family. The synthetic sequence consists of the preparation of a properly functionalized epoxygeraniol derivative, and its subsequent stereoselective cyclization mediated by Ti(III). This last step implies a domino process that starts with a homolytic epoxide opening followed by a radical cyclization and regioselective elimination. This concerted process gives access to the cyclohexane moiety with stereochemical control of five of its six carbon atoms. Full article
(This article belongs to the Special Issue Domino Reactions)
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514 KiB  
Article
Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and Coumarins
by Eito Yoshioka, Shigeru Kohtani and Hideto Miyabe
Molecules 2014, 19(1), 863-880; https://doi.org/10.3390/molecules19010863 - 13 Jan 2014
Cited by 21 | Viewed by 7300
Abstract
The domino three-component coupling reaction of arynes with DMF and active methylenes or methines was studied as a highly efficient method for preparing heterocycles. Coumarin derivative 5 was formed when diethyl malonate (2) or α-bromomalonate (3) were used as [...] Read more.
The domino three-component coupling reaction of arynes with DMF and active methylenes or methines was studied as a highly efficient method for preparing heterocycles. Coumarin derivative 5 was formed when diethyl malonate (2) or α-bromomalonate (3) were used as a C2-unit. In contrast, dihydrobenzofurans 7a and 7b were obtained by using α-chloroenolates generated from α-chloromalonates 4a and 4b and Et2Zn. The benzofuran 15a could be obtained by using ethyl iodoacetate (14) as a C1-unit. The one-pot conversion of dihydrobenzofurans 7a, 7b and 8a into benzofurans 15a and 15b was also studied. The direct synthesis of benzofuran 15b was achieved by using the active methine 18 having ketone and ester groups. Full article
(This article belongs to the Special Issue Domino Reactions)
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Review

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725 KiB  
Review
Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions
by Baskar Nammalwar and Richard A. Bunce
Molecules 2014, 19(1), 204-232; https://doi.org/10.3390/molecules19010204 - 24 Dec 2013
Cited by 113 | Viewed by 12044
Abstract
A review of the recent literature is given focusing on synthetic approaches to 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions. These syntheses involve: (1) reduction or oxidation followed by cyclization; (2) SNAr-terminated sequences; (3) acid-catalyzed ring closures [...] Read more.
A review of the recent literature is given focusing on synthetic approaches to 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions. These syntheses involve: (1) reduction or oxidation followed by cyclization; (2) SNAr-terminated sequences; (3) acid-catalyzed ring closures or rearrangements; (4) high temperature cyclizations and (5) metal-promoted processes as well as several less thoroughly studied reactions. Each domino method is presented with a brief discussion of mechanism, scope, yields, simplicity and potential utility. Full article
(This article belongs to the Special Issue Domino Reactions)
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