Abstract
A practical and environmentally benign synthesis of poly-substituted tetrahydropyrimidines from readily available starting materials has been developed. This process features an unprecedented intermolecular formal [3+3]-annulation of imines and 1,3,5-hexahydro-1,3,5-triazines under catalyst-free conditions. Importantly, differing from previous transformations, the 1,3,5-triazines are firstly utilized as formal 1,3-dipoles in cycloaddition reactions.
Highlights
A practical and environmentally benign synthesis of poly-substituted tetrahydropyrimidines from readily available starting materials has been developed
Inspired by Krische's work, we found that 1,3,5-triazines could be utilized as formal 1,4-dipoles in gold-catalyzed formal [4+1] and [4+3]-cycloaddition reactions to synthesize ve- and seven N-heterocycles.7a A erwards, we have successfully developed a series of 1,3,5-triazines involved [2+2+2],7b [2+1+2]7c,d and formal [4+3] annulations7e (Scheme 1c)
In continuation with our ongoing interest, we want to report here the rst use of 1,3,5triazines as formal 1,3-dipoles to react with imines, providing tetrahydropyrimidines in moderate to excellent yields under catalyst-free reaction conditions
Summary
Open Access Article. Published on 01 February 2018. Downloaded on 10/5/2020 1:34:56 PM. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Received 31st October 2017 Accepted 17th November 2017 DOI: 10.1039/c7ra11973a rsc.li/rsc-advances
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