Building Up a Piperazine Ring from a Primary Amino Group via Catalytic Reductive Cyclization of Dioximes Full article
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International Journal of Molecular Sciences
ISSN: 1661-6596 , E-ISSN: 1422-0067 |
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| Output data | Year: 2023, Volume: 24, Number: 14, Article number : 11794, Pages count : DOI: 10.3390/ijms241411794 | ||
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Abstract:
Piperazine is one of the most frequently found scaffolds in small-molecule FDA-approved drugs. In this study, a general approach to the synthesis of piperazines bearing substituents at carbon and nitrogen atoms utilizing primary amines and nitrosoalkenes as synthons was developed. The method relies on sequential double Michael addition of nitrosoalkenes to amines to give bis(oximinoalkyl)amines, followed by stereoselective catalytic reductive cyclization of the oxime groups. The method that we developed allows a straightforward structural modification of bioactive molecules (e.g., α-amino acids) by the conversion of a primary amino group into a piperazine ring.
Cite:
Pospelov E.V.
, Sukhorukov A.Y.
Building Up a Piperazine Ring from a Primary Amino Group via Catalytic Reductive Cyclization of Dioximes
International Journal of Molecular Sciences. 2023. V.24. N14. 11794 . DOI: 10.3390/ijms241411794 WOS Scopus OpenAlex
Building Up a Piperazine Ring from a Primary Amino Group via Catalytic Reductive Cyclization of Dioximes
International Journal of Molecular Sciences. 2023. V.24. N14. 11794 . DOI: 10.3390/ijms241411794 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:001036076600001 |
| Scopus: | 2-s2.0-85166012528 |
| OpenAlex: | W4385161735 |