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ID: past-exam-of-the-chemistry-course-of-the-year-4-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-1/9/b/ii/solution

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Past exam of the chemistry course of the year 4 of the natural sciences course of the University of Cambridge / 2022 / Paper 1 / 9 / b / ii / Solution by

Codex  0 2026-10-20

The analogous N-oxide rearrangement uses the carbon next to nitrogen that most readily supports addition and rearomatization. In isoquinoline this is C1. Thus replace the quinolin-2-yl group of D by isoquinolin-1-yl:

2-phenyl-3-(isoquinolin-1-yl)chromen-4-one .

(1)

The ynone-to-chromone atom mapping is unchanged. The change is attachment at isoquinoline C1, rather than copying quinoline numbering and assigning an isoquinolin-2-yl carbon substituent at the nitrogen position.

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