Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide
We studied the hydrazide compounds of the α-azidoacetyl group, which showed specific click reactivity by the intramolecular hydrogen bonding between the azido group and the N-H of the hydrazide moiety. In the competitive click reactions with a general alkyl azide, both traceless and non-traceless St...
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| Format: | Article |
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MDPI AG
2022-12-01
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| Series: | Organics |
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| Online Access: | https://www.mdpi.com/2673-401X/3/4/35 |
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| author | Hiroki Tanimoto Ryo Adachi Aoi Otsuki Takenori Tomohiro |
| author_facet | Hiroki Tanimoto Ryo Adachi Aoi Otsuki Takenori Tomohiro |
| author_sort | Hiroki Tanimoto |
| collection | DOAJ |
| description | We studied the hydrazide compounds of the α-azidoacetyl group, which showed specific click reactivity by the intramolecular hydrogen bonding between the azido group and the N-H of the hydrazide moiety. In the competitive click reactions with a general alkyl azide, both traceless and non-traceless Staudinger-Bertozzi ligation occurred azide-site-selectively by the acceleration effect of the hydrogen bonding. However, the product obtained from the traceless reaction was further transformed into heterocyclic compounds. In addition, in an attempt at a synthesis of naphthalimide-possessing azidoacetyl hydrazide, nitrogen-nitrogen bond cleavage of the azidoacetyl hydrazides occurred to give the reduced amine product. These unexpected results could help design molecules for the successful Staudinger-Bertozzi ligation of the hydrazide compounds and develop a new nitrogen-nitrogen bond cleavage method. |
| first_indexed | 2024-03-09T16:00:00Z |
| format | Article |
| id | doaj.art-1cf00aa8d3544d19966f94b80da99483 |
| institution | Directory Open Access Journal |
| issn | 2673-401X |
| language | English |
| last_indexed | 2024-03-09T16:00:00Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Organics |
| spelling | doaj.art-1cf00aa8d3544d19966f94b80da994832023-11-24T17:11:27ZengMDPI AGOrganics2673-401X2022-12-013452053310.3390/org3040035Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the HydrazideHiroki Tanimoto0Ryo Adachi1Aoi Otsuki2Takenori Tomohiro3Faculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanFaculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanFaculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanFaculty of Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, JapanWe studied the hydrazide compounds of the α-azidoacetyl group, which showed specific click reactivity by the intramolecular hydrogen bonding between the azido group and the N-H of the hydrazide moiety. In the competitive click reactions with a general alkyl azide, both traceless and non-traceless Staudinger-Bertozzi ligation occurred azide-site-selectively by the acceleration effect of the hydrogen bonding. However, the product obtained from the traceless reaction was further transformed into heterocyclic compounds. In addition, in an attempt at a synthesis of naphthalimide-possessing azidoacetyl hydrazide, nitrogen-nitrogen bond cleavage of the azidoacetyl hydrazides occurred to give the reduced amine product. These unexpected results could help design molecules for the successful Staudinger-Bertozzi ligation of the hydrazide compounds and develop a new nitrogen-nitrogen bond cleavage method.https://www.mdpi.com/2673-401X/3/4/35organic azidesstaudinger ligationnitrogen-nitrogen bond cleavagehydrogen-bonding interactionclick chemistry |
| spellingShingle | Hiroki Tanimoto Ryo Adachi Aoi Otsuki Takenori Tomohiro Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide Organics organic azides staudinger ligation nitrogen-nitrogen bond cleavage hydrogen-bonding interaction click chemistry |
| title | Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide |
| title_full | Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide |
| title_fullStr | Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide |
| title_full_unstemmed | Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide |
| title_short | Neighboring Nitrogen Atom-Induced Reactions of Azidoacetyl Hydrazides, including Unexpected Nitrogen-Nitrogen Bond Cleavage of the Hydrazide |
| title_sort | neighboring nitrogen atom induced reactions of azidoacetyl hydrazides including unexpected nitrogen nitrogen bond cleavage of the hydrazide |
| topic | organic azides staudinger ligation nitrogen-nitrogen bond cleavage hydrogen-bonding interaction click chemistry |
| url | https://www.mdpi.com/2673-401X/3/4/35 |
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