Azides in the Synthesis of Various Heterocycles
In this review, we focus on some interesting and recent examples of various applications of organic azides such as their intermolecular or intramolecular, under thermal, catalyzed, or noncatalyzed reaction conditions. The aforementioned reactions in the aim to prepare basic five-, six-, organometall...
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| Format: | Article |
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MDPI AG
2022-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/12/3716 |
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| author | AbdElAziz A. Nayl Ashraf A. Aly Wael A. A. Arafa Ismail M. Ahmed Ahmed I. Abd-Elhamid Esmail M. El-Fakharany Mohamed A. Abdelgawad Hendawy N. Tawfeek Stefan Bräse |
| author_facet | AbdElAziz A. Nayl Ashraf A. Aly Wael A. A. Arafa Ismail M. Ahmed Ahmed I. Abd-Elhamid Esmail M. El-Fakharany Mohamed A. Abdelgawad Hendawy N. Tawfeek Stefan Bräse |
| author_sort | AbdElAziz A. Nayl |
| collection | DOAJ |
| description | In this review, we focus on some interesting and recent examples of various applications of organic azides such as their intermolecular or intramolecular, under thermal, catalyzed, or noncatalyzed reaction conditions. The aforementioned reactions in the aim to prepare basic five-, six-, organometallic heterocyclic-membered systems and/or their fused analogs. This review article also provides a report on the developed methods describing the synthesis of various heterocycles from organic azides, especially those reported in recent papers (till 2020). At the outset, this review groups the synthetic methods of organic azides into different categories. Secondly, the review deals with the functionality of the azido group in chemical reactions. This is followed by a major section on the following: (1) the synthetic tools of various heterocycles from the corresponding organic azides by one-pot domino reaction; (2) the utility of the chosen catalysts in the chemoselectivity favoring C−H and C-N bonds; (3) one-pot procedures (i.e., Ugi four-component reaction); (4) nucleophilic addition, such as Aza-Michael addition; (5) cycloaddition reactions, such as [3+2] cycloaddition; (6) mixed addition/cyclization/oxygen; and (7) insertion reaction of C-H amination. The review also includes the synthetic procedures of fused heterocycles, such as quinazoline derivatives and organometal heterocycles (i.e., phosphorus-, boron- and aluminum-containing heterocycles). Due to many references that have dealt with the reactions of azides in heterocyclic synthesis (currently more than 32,000), we selected according to generality and timeliness. This is considered a recent review that focuses on selected interesting examples of various heterocycles from the mechanistic aspects of organic azides. |
| first_indexed | 2024-03-09T22:55:53Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T22:55:53Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1ab3d0a2382c4e93a843a0b7b67e408b2023-11-23T18:09:59ZengMDPI AGMolecules1420-30492022-06-012712371610.3390/molecules27123716Azides in the Synthesis of Various HeterocyclesAbdElAziz A. Nayl0Ashraf A. Aly1Wael A. A. Arafa2Ismail M. Ahmed3Ahmed I. Abd-Elhamid4Esmail M. El-Fakharany5Mohamed A. Abdelgawad6Hendawy N. Tawfeek7Stefan Bräse8Department of Chemistry, College of Science, Jouf University, Sakaka 72341, Al Jouf, Saudi ArabiaChemistry Department, Faculty of Science, Organic Division, Minia University, El-Minia 61519, EgyptDepartment of Chemistry, College of Science, Jouf University, Sakaka 72341, Al Jouf, Saudi ArabiaDepartment of Chemistry, College of Science, Jouf University, Sakaka 72341, Al Jouf, Saudi ArabiaComposites and Nanostructured Materials Research Department, Advanced Technology and New Materials Research Institute, City of Scientific Research and Technological Applications (SRTA-City), Alexandria 21934, EgyptProtein Research Department, Genetic Engineering and Biotechnology Research Institute GEBRI, City of Scientific Research and Technological Applications (SRTA City), New Borg Al-Arab, Alexandria 21934, EgyptDepartment of Pharmaceutical Chemistry, College of Pharmacy, Jouf University, Sakaka 72341, Al Jouf, Saudi ArabiaChemistry Department, Faculty of Science, Organic Division, Minia University, El-Minia 61519, EgyptInstitute of Organic Chemistry, Karlsruhe Institute of Technology, 76131 Karlsruhe, GermanyIn this review, we focus on some interesting and recent examples of various applications of organic azides such as their intermolecular or intramolecular, under thermal, catalyzed, or noncatalyzed reaction conditions. The aforementioned reactions in the aim to prepare basic five-, six-, organometallic heterocyclic-membered systems and/or their fused analogs. This review article also provides a report on the developed methods describing the synthesis of various heterocycles from organic azides, especially those reported in recent papers (till 2020). At the outset, this review groups the synthetic methods of organic azides into different categories. Secondly, the review deals with the functionality of the azido group in chemical reactions. This is followed by a major section on the following: (1) the synthetic tools of various heterocycles from the corresponding organic azides by one-pot domino reaction; (2) the utility of the chosen catalysts in the chemoselectivity favoring C−H and C-N bonds; (3) one-pot procedures (i.e., Ugi four-component reaction); (4) nucleophilic addition, such as Aza-Michael addition; (5) cycloaddition reactions, such as [3+2] cycloaddition; (6) mixed addition/cyclization/oxygen; and (7) insertion reaction of C-H amination. The review also includes the synthetic procedures of fused heterocycles, such as quinazoline derivatives and organometal heterocycles (i.e., phosphorus-, boron- and aluminum-containing heterocycles). Due to many references that have dealt with the reactions of azides in heterocyclic synthesis (currently more than 32,000), we selected according to generality and timeliness. This is considered a recent review that focuses on selected interesting examples of various heterocycles from the mechanistic aspects of organic azides.https://www.mdpi.com/1420-3049/27/12/3716organic azidesclick reactioncatalysisfive membered ringssix membered ringsorgano-metal heterocycles |
| spellingShingle | AbdElAziz A. Nayl Ashraf A. Aly Wael A. A. Arafa Ismail M. Ahmed Ahmed I. Abd-Elhamid Esmail M. El-Fakharany Mohamed A. Abdelgawad Hendawy N. Tawfeek Stefan Bräse Azides in the Synthesis of Various Heterocycles Molecules organic azides click reaction catalysis five membered rings six membered rings organo-metal heterocycles |
| title | Azides in the Synthesis of Various Heterocycles |
| title_full | Azides in the Synthesis of Various Heterocycles |
| title_fullStr | Azides in the Synthesis of Various Heterocycles |
| title_full_unstemmed | Azides in the Synthesis of Various Heterocycles |
| title_short | Azides in the Synthesis of Various Heterocycles |
| title_sort | azides in the synthesis of various heterocycles |
| topic | organic azides click reaction catalysis five membered rings six membered rings organo-metal heterocycles |
| url | https://www.mdpi.com/1420-3049/27/12/3716 |
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