Syntheses of 1,2,3,4-tetrahydroisoquinolines from N-sulfonylphenethylamines and aldehydes.

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N-Sulfonylphenethylamines (6-9) have been readily condensed with formaldehyde under mild acidic condition to the corresponding N-sulfonyl-1, 2, 3, 4-tetrahydroisoquinolines (14-17) in excellent yields. Condensation of sulfonamide (10) with formaldehyde under similar condition gave a mixture of two cyclization products (18 and 19). In the case of similar condensation of 3, 4-disubstituted-N-sulfonamides (11 and 12) with formaldehyde, 6, 7-disubstituted products (20 and 21) were obtained alone. Similar reaction of sulfonamides (6, 11 and 12) with aliphatic aldehydes or aromatic aldehydes also afforded the corresponding N-tosyl-1, 2, 3, 4-tetrahydroisoquinolines (22-27). Furthermore, 1-benzyl-N-tosyl-1, 2, 3, 4-tetrahydroisoquinolines (31 and 37) were similarly synthesized from sulfonamide (12 or 13) and phenyl acetaldehyde (30 or 36). Birch reduction of (37) afforded the racemic form (33) of natural N-nororientaline, which was previously isolated by us from the leaves of Erythrina X bidwillii (Leguminosae).

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