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15.5.1.1.1.1.1.1.1 Variation 1: From 2-Formylbenzylcarbonyl Compounds

DOI: 10.1055/sos-SD-015-01146

Álvarez, M.; Joule, J. A.Science of Synthesis, (200515665.

The interaction between ammonia and a (2-formylphenyl)acetaldehyde 21 leads directly to an isoquinoline 22 with no substituents on the heterocyclic ring (Scheme 9). The di­aldehyde precursors 21 can be conveniently obtained via ozonolysis of indenes 20 and the sequence is conveniently carried out without isolation of intermediates.[‌28‌] Dihydrox­y­lation using osmium(VIII) oxide and then periodate cleavage can also be used to access the (2-formylphenyl)acetaldehydes 21.[‌29‌]

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