Biogenetically inspired synthesis of marine C6N4 2-aminoimidazole alkaloids: ab initio calculations, tautomerism, and reactivity

…, MT Martin, ETH Dau, N Travert, A Al-Mourabit

Index: Abou-Jneid, Robert; Ghoulami, Said; Martin, Marie-Therese; Dau, Elise Tran Huu; Travert, Nathalie; Al-Mourabit, Ali Organic Letters, 2004 , vol. 6, # 22 p. 3933 - 3936

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Citation Number: 32

Abstract

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. ...