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10.24.2.2.2 Synthesis from 3-(Pyrimidin-2-yl)-1,2,4-triazines and Benzyne

DOI: 10.1055/sos-SD-110-01955

Harris, P. A.Science of Synthesis Knowledge Updates, (20213107.

The reaction between 3-(pyrimidin-2-yl)-1,2,4-triazines 85 and benzyne, generated in situ from 2-aminobenzoic acid and 3-methylbutyl nitrite (isoamyl nitrite), results in the formation of 10-(1H-1,2,3-triazol-1-yl)pyrimido[1,2-a]indoles 86 (Scheme 22).[‌24‌] The reaction mechanism involves a [2 + 3] cycloaddition of benzyne to substrate 85 and subsequent rearrangement, and this, plus an experimental procedure, is described in Section 10.24.1.2.1 for the analogous formation of pyrido[1,2-a]indoles.

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