Aminonaphthalene derivative, synthesis

Scheme 23 Synthesis of intermediate 89 used in the preparation of gram quantities of an aminonaphthalene derivative 91.

Canete, A. Melendrez, M. X. Saitz, C. Zanocco, A. L. Synthesis of aminonaphthalene derivatives using the Bucherer reaction under microwave irradiation. Synth. Commun. 2001, 31, 2143-2148. 

Reaction of chromium carbene complex 170 (Scheme 17.23) with isonitriles led to aminonaphthalene derivatives (e.g., 172) [70]. This transformation was a key step for the total synthesis of the calphostin natural products. The crude aminophenol was treated with cerium(IV) to afford the o-quinone derivative. The photochemical... 

As 2-aminonaphthalene 125 can provide an enamine-like reactivity, Pashkovskii et al. nsed this compound for the synthesis of tetracyclic 1,4-dihydropyridine derivatives 126 starting from tetronic acid 123 and several aryl aldehydes 124 (Scheme 13.35) [56]. The reactions were conducted in refluxing ethanol within 30-60min and the desired products 126 could be obtained in moderate to good yields (47-84%). 

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