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Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis.

ABSTRACT: Prebiotically plausible ferrocyanide-ferricyanide photoredox cycling oxidatively converts thiourea to cyanamide, whilst HCN is reductively homologated to intermediates which either react directly with the cyanamide giving 2-aminoazoles, or have the potential to do so upon loss of HCN from the system. Thiourea itself is produced by heating ammonium thiocyanate, a product of the reaction of HCN and hydrogen sulfide under UV irradiation.

SUBMITTER: Liu Z

PROVIDER: S-EPMC7808312 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis.

Liu Ziwei Z Wu Long-Fei LF Bond Andrew D AD Sutherland John D JD

Chemical communications (Cambridge, England) 20201014 88

Prebiotically plausible ferrocyanide-ferricyanide photoredox cycling oxidatively converts thiourea to cyanamide, whilst HCN is reductively homologated to intermediates which either react directly with the cyanamide giving 2-aminoazoles, or have the potential to do so upon loss of HCN from the system. Thiourea itself is produced by heating ammonium thiocyanate, a product of the reaction of HCN and hydrogen sulfide under UV irradiation. ...[more]

PMID: 33151212

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