Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 7, Pages 5380-5387Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00052
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- SERB, New Delhi
- UGC
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The newly developed reaction method involves the [4+1]-annulation of in situ generated heterocyclic azine-aldimines with beta-keto sulfoxonium ylides, resulting in the construction of N-fused imidazole rings. The ylides act as a nucleophilic 1,1-dipolar one-carbon synthon and a source of an internal oxidant, dimethyl sulfoxide, promoting in situ dehydrogenation to product scaffolds. This approach enables the synthesis of imidazo-pyridine, pyrazine, and pyrimidine heteroaromatics.
A new [4+1]-annulation of in situ generated heterocyclic azine-aldimines with beta-keto sulfoxonium ylides has been developed. The reaction constructs N-fused imidazole rings. In the reaction, the ylides play a dual-functional role of a nucleophilic 1,1-dipolar one-carbon synthon and a source of an internal oxidant, dimethyl sulfoxide, that promotes in situ dehydrogenation to product scaffolds. The method enables access to imidazo-pyridine, pyrazine, and pyrimidine heteroaromatics.
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