Fig. 1: Three-dimensional scaffold mimetics of heteroaromatic rings, showing state of the art and reaction design using anti-rule-of-five intramolecular aza-Paternò–Büchi reaction. | Nature Synthesis

Fig. 1: Three-dimensional scaffold mimetics of heteroaromatic rings, showing state of the art and reaction design using anti-rule-of-five intramolecular aza-Paternò–Büchi reaction.

From: Breaking the ‘rule-of-five’ to access bridged bicyclic heteroaromatic bioisosteres

Fig. 1: Three-dimensional scaffold mimetics of heteroaromatic rings, showing state of the art and reaction design using anti-rule-of-five intramolecular aza-Paternò–Büchi reaction.

a, Three-dimensional (3D) bioisosteres of substituted (hetero)aromatic rings. b, Exit vector analyses of N-heterocycles. D2-3, distance between carbon atoms 2 and 3; θ, angle between C2–C3 atoms and H1–C2; φ, angle between H4–C3 and H1–C2. c, Selectivity in intramolecular aza-Paternò–Büchi reactions39,47,48. d, DFT calculations: breaking the rule-of-five. Fsp3, fraction of sp3-hybridized carbon atoms; Ts, p-toluenesulfonyl; TS, transition state; k, rate constant.

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