Journal article
Secondary products from intramolecular cycloadditions of azidoalkyl enol ethers and azidoalkyl vinyl bromides. 1-Azadienes, their reactions with diphenylketene, and radical cyclizations to form bi- and tricyclic lactams
- Abstract:
- Azidoalkyl enol ethers undergo intramolecular 1,3-dipolar cycloaddition to generate stable triazolines; in contrast, the cycloadducts formed by heating analogous azidoalkyl vinyl bromides are unstable with respect to elimination of N2 and HBr, affording 1-azadienes (2-alkenyl cyclic imines). These primary products may be isolated or treated directly with diphenylketene to produce bi- and tri-cyclic 3,4-dihydropyridin-2(1H)-ones; similar ring systems may also be produced from the azadienes by N-acylation and radical cyclization.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
-
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(Preview, Accepted manuscript, pdf, 639.4KB, Terms of use)
-
- Publisher copy:
- 10.1021/acs.joc.9b02005
Authors
Bibliographic Details
- Publisher:
- American Chemical Society
- Journal:
- Journal of Organic Chemistry More from this journal
- Volume:
- 84
- Issue:
- 21
- Pages:
- 13780-13793
- Publication date:
- 2019-09-23
- Acceptance date:
- 2019-09-23
- DOI:
- EISSN:
-
1520-6904
- ISSN:
-
0022-3263
Item Description
- Language:
-
English
- Pubs id:
-
pubs:1055423
- UUID:
-
uuid:20a8911d-469c-4255-956c-edf8ab9aa08a
- Local pid:
-
pubs:1055423
- Source identifiers:
-
1055423
- Deposit date:
-
2019-09-24
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2019
- Rights statement:
- Copyright © 2019 American Chemical Society
- Notes:
-
This is the accepted manuscript version of the article. The final version is available from American Chemical Society at https://doi.org/10.1021/acs.joc.9b02005
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