Fine bubble technology for the green synthesis of fairy chemicals.

Org Biomol Chem

Department of Optoelectronics and Nanostructure Science, Graduate School of Science and Technology, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan.

Published: May 2024

Fairy chemicals (FCs), such as 2-azahypoxanthine (AHX), are a potential new class of plant hormones that are naturally present in plants and produced a novel purine metabolic pathway. FCs support plant resilience against various stresses and regulate plant growth. In this study, we developed a four-step method for synthesising AHX from 2-cyanoacetamide, achieving a good yield. Oxime was obtained from 2-cyanoacetamide the oximation reaction. Cascade-type one-pot selective Pt/C-catalysed reduction of oxime, followed by a coupling reaction with formamidine acetate, yielded intermediate 5-amino-1-imidazole-4-carboxamide (AICA). For the synthesis of AICA from oxime, we used modern fine bubble technology, affording AICA in 69% yield. Subsequently, we synthesised 4-diazo-4-imidazole-5-carboxamide (DICA) from AICA the diazotisation reaction. Notably, the synthesis of DICA from AICA was achieved, and the stability of previously known less stable DICA in the solid state was confirmed. Finally, PhI(OAc) (0.5 mol%) catalysed the intramolecular cyclisation of DICA in the green solvent water to yield AHX (overall yield of 47%). This study's innovative techniques and substantial discoveries highlight its potential influence and significance in FC science, thereby establishing a new standard for subsequent research.

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Source
http://dx.doi.org/10.1039/d4ob00237gDOI Listing

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