Synthesis of Guanidine Derivatives and Molecular Recognition

Qi, Yanxing; Gao, Haixiang; Yang, Min; Xia, Chungu; Suo, Jishuan

doi:10.1081/scc-120017128

Cited by 7 publications

(1 citation statement)

References 12 publications

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“…On the basis of this result, other substituted guanidines were surveyed in order to identify a protected guanidine that would both participate in Biginelli condensations and allow subsequent deprotection to be accomplished efficiently. Neither Boc-guanidine nor p -tosylguanidine were reactive in Biginelli condensations using numerous reaction conditions (acidic, basic, Lewis acidic) . The reduced basicity of these guanidines compared to N , N -diallylguanidine likely accounts for this lack of reactivity .…”

Section: Resultsmentioning

confidence: 97%

Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

Nilsson

Overman

2006

J. Org. Chem.

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Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the 3-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a β-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a 4-step sequence. The second method utilizes a triazone-protected guanidine, a β-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a 2-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

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Section: Resultsmentioning

confidence: 97%