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Thiaazadienes (2a–e), selenoazadienes (6a–f), Barton selenium esters (8a–e) and Barton sulphur esters (10a–d) react with 2,3-didehydronaphthalene (4) generated from (phenyl)[(3trimethylsilyl)-2-naphthyl]iodonium triflate (3) at 0°C to give 4H-naphtho[2,3-e]-1,3-thiazines (5a-e), 4H-naphtho[2,3-e]-1,3-selenazines (7a-f), naphtho[2',3':4,5]selenolo[2,3-b]pyridines (9ae) and naphtho[2',3':4,5]thieno[2,3-b]pyridines (11a-d).

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Facile synthesis of 4H-naphtho[2,3-e] derivatives of 1,3-thiazines and 1,3-selenazines and naphtho[2',3':4,5] derivatives of selenolo[2,3-b]pyridines and thieno[2,3-b]pyridines via 2,3-didehydronaphthalene