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Synthesis 2021; 53(12): 2133-2141
DOI: 10.1055/a-1360-9852
DOI: 10.1055/a-1360-9852
paper
Efficient Route for the Synthesis of Diverse Heteroannelated 5-Cyanopyridines
The work was funded by Enamine Ltd. and supported by the Ministry of Education and Science of Ukraine (Grant Number 0120U102179).
Abstract
The new efficient, convenient protocol for the synthesis of heteroannelated 3-cyanopyridines and pyrimidines starting from diverse aminoheterocycles and 3,3-dimethoxy-2-formylpropionitrile sodium salt was elaborated. The advantages and improvements of the procedure compared to previously known methods are shown. The scope and limitations of the method are determined. The impact of the structural features on regioselectivity are discussed. The preparativeness, scalability, and application scope of the elaborated protocol are demonstrated by the synthesis of five heteroannelated 3-cyanopyridines in quantities up to 100 grams.
Key words
aminoheterocycles - heterocyclization - heteroannelated 3-cyanopyridines - heteroannelated 3-cyanopyrimidines - 2-dimethoxy-3-hydroxyacrylonitrileSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1360-9852.
- Supporting Information
- CIF File
Publication History
Received: 21 September 2020
Accepted after revision: 18 January 2021
Accepted Manuscript online:
18 January 2021
Article published online:
08 February 2021
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