Journal article
A three-component Ugi-type reaction of N-carbamoyl imines enables a broad scope primary α-amino 1,3,4-oxadiazole synthesis
- Abstract:
- A general synthesis of N-protected primary α-amino 1,3,4-oxadiazoles, from N-carbamoyl imines, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids, is described. Featuring an isocyanide addition reaction with N-carbamoyl imines, this efficient three-component Ugi-type reaction was found to be broad in scope with respect to imine, and carboxylic acid coupling partners. Furthermore, the versatility of this method was demonstrated by α-amino 1,2,4-triazole synthesis, the late-stage functionalization of seven drug molecules, and five divergent derivatizations of a primary α-amino 1,3,4-oxadiazole.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
-
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(Preview, Accepted manuscript, pdf, 1.1MB, Terms of use)
-
- Publisher copy:
- 10.1021/acs.orglett.1c02945
Authors
+ Engineering and Physical Sciences Research Council
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- Funder identifier:
- http://dx.doi.org/10.13039/501100000266
- Grant:
- EP/J013501/1
- Publisher:
- American Chemical Society
- Journal:
- Organic Letters More from this journal
- Volume:
- 23
- Issue:
- 21
- Pages:
- 8209-8213
- Publication date:
- 2021-10-11
- Acceptance date:
- 2021-10-11
- DOI:
- EISSN:
-
1523-7052
- ISSN:
-
1523-7060
- Pmid:
-
34633203
- Language:
-
English
- Keywords:
- Pubs id:
-
1200262
- Local pid:
-
pubs:1200262
- Deposit date:
-
2021-10-21
- ARK identifier:
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2021
- Rights statement:
- © 2021 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.orglett.1c02945
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