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Diazo Chemistry
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Diazo Chemistry

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

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 10578

Special Issue Editors

Prof. Dr. Mikhail Krasavin

E-Mail Website
Guest Editor
Institute of Chemistry, Saint Petersburg State University, Saint Petersburg, Russia
Interests: organic synthesis; chemistry of heterocyclic compounds; diazo chemistry; medicinal chemistry; privileged motifs for drug discovery
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Dmitry Dar’in

E-Mail Website
Guest Editor
Institute of Chemistry, Saint Petersburg State University, Saint Petersburg, Russia
Interests: organic synthesis; chemistry of heterocyclic compounds; diazo chemistry; medicinal chemistry; privileged motifs for drug discovery
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

As an organic moiety consisting of two linked nitrogen atoms azo at the terminal position, diazo compounds were first produced by Peter Griess, who discovered a versatile new chemical reaction. The early application of diazonium compounds in multi-component reactions (MCRs) can be traced back to 1,3-dipolar cycloaddition reactions via metal carbene, which has been widely used and applied in the synthesis of various oxygen/nitrogen heterocyclic compounds. Today, the involvement of diazo in multicomponent reactions captured by active intermediates has been gradually recognized by chemists. For a century, progress has been made generally in asymmetric catalysis of such reactions. This is also one of the fields of diazo chemistry that is still worthy of continuous exploration.

This Special Issue welcomes the submission of unpublished manuscripts (original research papers or review articles) on all aspects of diazo chemistry and any organic synthesis that diazonium compounds involved.

It is a great pleasure to invite you to submit a contribution on any of these aspects.

Prof. Dr. Mikhail Krasavin
Prof. Dr. Dmitry Dar’in
Guest Editors

Manuscript Submission Information

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. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short 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 thoroughly refereed through a single-blind 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 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Diazo compounds
  • Catalysis
  • Multi-component reactions
  • Photolysis
  • Rearrangements
  • Scaffold-oriented synthesis
  • Heterocycle construction
  • Cascade transformation
  • Metal carbene

Published Papers (3 papers)

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Research

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15 pages, 2877 KiB  
Article
Isomerization of 5-(2H-Azirin-2-yl)oxazoles: An Atom-Economic Approach to 4H-Pyrrolo[2,3-d]oxazoles
by Timur O. Zanakhov, Ekaterina E. Galenko, Mariya A. Kryukova, Mikhail S. Novikov and Alexander A. Khlebnikov
Molecules 2021, 26(7), 1881; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26071881 - 26 Mar 2021
Cited by 3 | Viewed by 2041
Abstract
An atom economical method for the preparation of variously substituted 4H-pyrrolo[2,3-d]oxazoles was developed on the basis of thermal isomerization of 5-(2H-azirin-2-yl)oxazoles. The latter were prepared by Rh2(oct)4 catalyzed reaction of 2-(3-aryl/heteroaryl)-2-diazoacetyl-2H-azirines with [...] Read more.
An atom economical method for the preparation of variously substituted 4H-pyrrolo[2,3-d]oxazoles was developed on the basis of thermal isomerization of 5-(2H-azirin-2-yl)oxazoles. The latter were prepared by Rh2(oct)4 catalyzed reaction of 2-(3-aryl/heteroaryl)-2-diazoacetyl-2H-azirines with a set of substituted acetonitriles, benzonitriles, acrylonitrile and fumaronitrile. According to DFT calculations the transformation of 5-(2H-azirin-2-yl)oxazole to 4H-pyrrolo[2,3-d]oxazole occurs through the nitrenoid-like transition state to give a 3aH-pyrrolo[2,3-d]oxazole intermediate, followed by 1,5-H-shift. Full article
(This article belongs to the Special Issue Diazo Chemistry)
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Review

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74 pages, 55175 KiB  
Review
Multicomponent Reactions Involving Diazo Reagents: A 5-Year Update
by Olga Bakulina, Anna Inyutina, Dmitry Dar’in and Mikhail Krasavin
Molecules 2021, 26(21), 6563; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216563 - 29 Oct 2021
Cited by 16 | Viewed by 3356
Abstract
This review summarizes recent developments in multicomponent reactions of diazo compounds. The role of diazo reagent and the type of interaction between components was analyzed to structure the discussion. In contrast to previous reviews on related topics mostly focused on metal catalyzed transformations, [...] Read more.
This review summarizes recent developments in multicomponent reactions of diazo compounds. The role of diazo reagent and the type of interaction between components was analyzed to structure the discussion. In contrast to previous reviews on related topics mostly focused on metal catalyzed transformations, a substantial amount of organocatalytic or catalyst-free methodologies is covered in this work. Full article
(This article belongs to the Special Issue Diazo Chemistry)
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70 pages, 20666 KiB  
Review
Diazocarbonyl and Related Compounds in the Synthesis of Azoles
by Anton Budeev, Grigory Kantin, Dmitry Dar’in and Mikhail Krasavin
Molecules 2021, 26(9), 2530; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092530 - 26 Apr 2021
Cited by 14 | Viewed by 4317
Abstract
Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A [...] Read more.
Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles. Full article
(This article belongs to the Special Issue Diazo Chemistry)
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