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A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N‐oxyl radical (PINO) generated from N‐hydroxyphthalimide by air oxygen and Co(II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromatic base, which is then rearo‐matised in a chain process. Quinazoline has an anomalous behaviour, giving 3H‐quinazolin‐4‐one as the only reaction product.
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Minisci et al. (2003) studied this question.
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