Formal [2+2+2] Cycloaddition Reaction of 1,3,5‐Triazinanes with diethyl acetylene dicarboxylate: Approach to Tetrahydropyrimidines

An unprecedented [2+2+2] cycloaddition reaction of 1,3,5‐triazinanes with diethyl acetylene dicarboxylate is disclosed. This catalyst free reaction provided an efficient and mild approach to synthesize a variety of functionalized tetrahydropyrimidines in moderate to excellent yields (up to 99 % yiel...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-11, Vol.2021 (44), p.5941-5945
Main Authors: Shi, Ruijie, Gao, Limei, Chen, Weiji, Shi, Yangqing, Cao, Zhixing, Zheng, Yongsheng, Liu, Jikai
Format: Article
Language:English
Subjects:
1,3,5-Triazinanes
Acetylene
Alkynes
Cycloaddition
Cycloadditions
Synthetic methods
Tetrahydropyrimidines
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Summary:An unprecedented [2+2+2] cycloaddition reaction of 1,3,5‐triazinanes with diethyl acetylene dicarboxylate is disclosed. This catalyst free reaction provided an efficient and mild approach to synthesize a variety of functionalized tetrahydropyrimidines in moderate to excellent yields (up to 99 % yield). Preliminary mechanistic investigation has been conducted to elucidate the reaction process. An unprecedented [2+2+2] cycloaddition reaction of 1,3,5‐triazinanes with diethyl acetylene dicarboxylate for the synthesis of functionalized tetrahydropyrimidines has been developed under metal‐free conditions. Preliminary mechanistic investigation has been conducted to elucidate the reaction process.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101233