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Naphtho[1′,2′:5,6]pyrano[2,3–6][1,5]benzodiazepine Derivatives

1981; Wiley; Volume: 18; Issue: 8 Linguagem: Inglês

10.1002/jhet.5570180827

1943-5193

G. ROMA, A. ERMILI, Alessandro Balbi, Elda Massa, Mario Di Braccio,

Synthesis of heterocyclic compounds

Abstract The reaction of 3‐(dimethylamino)‐1‐oxo‐1 H ‐naphtho[2,1‐ b ]pyran‐2‐carbaldehyde (Ia) with o ‐phenylenediamines or N ‐monosubstituted o ‐phenylenediamines in refluxing glacial acetic acid afforded the corresponding naphtho[1′,2′:5,6]pyrano[2,3‐ b ][1,5]benzodiazepin‐15‐(8 H )ones V in very good yields. A similar result was achieved when the reaction was carried out in refluxing pyridine, using N ‐monosubstituted o ‐phenylenediamine hydrochlorides. The isolation of a significant intermediate as well as the synthesis through a different univocal pathway confirmed the structure of the compounds V. Moreover the reaction of Ia with N ‐monosubstituted o ‐phenylenediamines in refluxing pyridine generally afforded only low yields of compounds V, sometimes together with naphtho[1′,2′:5,6]pyrano[2,3‐ b ][1,5]benzodiazepin‐15‐(13 H )ones VII, isomers of V.