Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids:: Ab initio calculations, tautomerism, and reactivity
Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids:: Ab initio calculations, tautomerism, and reactivity
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DOI：
10.1021/ol048529e
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发表时间：
2004-10-28
期刊：
影响因子：
5.2
通讯作者：
Al-Mourabit, A
中科院分区：
文献类型：
--
作者：
Abou-Jneid, R;Ghoulami, S;Al-Mourabit, A
[图解]在溴存在下，通过保护的胍与N-甲氧基-1，2-二氢吡啶的选择性加成，完成了稠合四氢-咪唑并吡啶13的简单合成。4-取代的2-氨基咪唑14是一种新的合成方法。用这种新方法可以从吡啶合成天然海洋代谢物3-氨基-1-(2-氨基咪唑-4-基)-丙烯-1-烯(1)及其衍生物。对互变构体I-IV的能量进行从头算计算，并通过氢化实验提供了对它们的反应性的洞察。
[GRAPHICS]A simple synthesis of the fused tetrahydro-imidazopyridine 13 was accomplished via selective addition of protected guanidine to N-carbomethoxy-1,2-dihydropyridine in the presence of bromine. Base-mediated semicleavage of the aminal gave 4-substituted 2-aminoimidazole 14. With this new method, natural marine metabolite 3-amino-1-(2-aminoimidazol-4-yl)-prop-1-ene (1) and derivatives may now be prepared from pyridine. Ab initio calculations of the energies of tautomers I-IV and deuteration experiments have provided insight into their reactivity.