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Tytuł pozycji:

Diazophosphonates: Effective Surrogates for Diazoalkanes in Pyrazole Synthesis.

Tytuł:
Diazophosphonates: Effective Surrogates for Diazoalkanes in Pyrazole Synthesis.
Autorzy:
Ruffell K; School of Chemistry, University of Nottingham University Park, Nottingham, NG7 2RD, U.K.
Smith FR; School of Chemistry, University of Nottingham University Park, Nottingham, NG7 2RD, U.K.
Green MT; School of Chemistry, University of Nottingham University Park, Nottingham, NG7 2RD, U.K.
Nicolle SM; School of Chemistry, University of Nottingham University Park, Nottingham, NG7 2RD, U.K.
Inman M; School of Chemistry, University of Nottingham University Park, Nottingham, NG7 2RD, U.K.
Lewis W; School of Chemistry, University of Nottingham University Park, Nottingham, NG7 2RD, U.K.
Hayes CJ; School of Chemistry, University of Nottingham University Park, Nottingham, NG7 2RD, U.K.
Moody CJ; School of Chemistry, University of Nottingham University Park, Nottingham, NG7 2RD, U.K.
Źródło:
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2021 Oct 01; Vol. 27 (55), pp. 13703-13708. Date of Electronic Publication: 2021 Sep 08.
Typ publikacji:
Journal Article
Język:
English
Imprint Name(s):
Original Publication: Weinheim, Germany : Wiley-VCH
MeSH Terms:
Alkynes*
Pyrazoles*
Cycloaddition Reaction ; Hydrazones
References:
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Grant Information:
EP/L015633/1 Engineering and Physical Sciences Research Council; BB/M008770/1 United Kingdom BB_ Biotechnology and Biological Sciences Research Council
Contributed Indexing:
Keywords: 1,5-sigmatropic rearrangements; diazophosphonates; dipolar cycloaddition; pyrazoles
Substance Nomenclature:
0 (Alkynes)
0 (Hydrazones)
0 (Pyrazoles)
3QD5KJZ7ZJ (pyrazole)
Entry Date(s):
Date Created: 20210823 Date Completed: 20211005 Latest Revision: 20211005
Update Code:
20240105
DOI:
10.1002/chem.202101788
PMID:
34425034
Czasopismo naukowe
Diazophosphonates, readily prepared from α-ketophosphonates by oxidation of the corresponding hydrazones in batch or in flow, are useful partners in 1,3-dipolar cycloaddition reactions to alkynes to give N-H pyrazoles, including the first intramolecular examples of such a process. The phosphoryl group imbues a number of desirable properties into the diazo 1,3-dipole. The electron-withdrawing nature of the phosphoryl stabilizes the diazo compound making it easier to handle, whilst the ability of the phosphoryl group to migrate readily in a [1,5]-sigmatropic rearrangement enables its transfer from C to N to aromatize the initial cycloadduct, and hence its facile removal from the final pyrazole product. Overall, the diazophosphonate acts as a surrogate for the much less stable diazoalkane in cycloadditions, with the phosphoryl group playing a vital, but traceless, role. The cycloaddition proceeds more readily with alkynes bearing electron-withdrawing groups, and is regiospecific with asymmetrical alkynes. The potential of diazophosphonates for use in bioorthogonal cycloadditions is demonstrated by their facile addition to strained alkynes.
(© 2021 Wiley-VCH GmbH.)
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