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Synthesis 2020; 52(08): 1266-1272
DOI: 10.1055/s-0039-1690802
DOI: 10.1055/s-0039-1690802
paper
Realizing the Trifunctional Potential of Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Convenient Assembly of 6,7-Dihydro-4H-[1,2,3]triazolo[5,1-c][1,4]thiazine Core
This research was supported by the Russian Science Foundation (project grant 19-75-30008). The authors declare no competing financial interest.Further Information
Publication History
Received: 16 December 2019
Accepted after revision: 03 January 2020
Publication Date:
27 January 2020 (online)
Abstract
The first example of exploiting the trifunctional character of alkyl 4-chloro-2-diazo-3-oxobutanoates in the reactions with vicinal N,S-bis-nucleophiles leading to the formation of bicyclic 6,7-dihydro-4H-[1,2,3]triazolo[5,1-c][1,4]thiazines is presented. The key to the successful realization of the atom-economical synthetic strategy is the initial S N 2 event, which facilitates the subsequent domino 1,2,3-triazole formation via the Wolff reaction. Equally important is the choice of sodium acetate as the base: acetic acid formed in the course of the initial nucleophilic substitution acts as an efficient catalyst for the Wolff reaction, which suppresses the competing, unwanted fragmentation path (observed when other bases are used).
Key words
diazo transfer - multicenter reactions - nucleophilic substitution - domino reactions - Wolff 1,2,3-triazole synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690802. Experimental procedures, analytical data, copies of the 1H and 13C NMR spectra, and X-ray crystallographic data are included.
- Supporting Information
- CIF File
-
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