Base-mediated hydrolytic cleavage with chain migration of 1-chloromethyl-tetrahydropyrano[3,4-b]indoles: an unusual pathway to 2-succinoyl tryptophols

Tetrahedron Letters

Volumn 47, Issue 34, 2006, Pages 6045-6048

  Chou, Shan Yen ^a   Chen, Ching Hui ^a  

^a DEVELOPMENT CENTER FOR BIOTECHNOLOGY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1 CHLOROMETHYL ISOCHROMAN; BASE; INDOLE DERIVATIVE; ISOCHROMAN DERIVATIVE; TRYPTOPHOL; UNCLASSIFIED DRUG; WATER;

ARTICLE; HEATING;

EID: 33746295896     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.105     Document Type: Article

References (19)

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15. The synthesis of 1 and structurally related 1-chloromethyl-tetrahydropyrano[3,4-b]indoles (6-10) has been described in our earlier article, see Ref. 14.
16. 2: C, 63.05; H, 5.62; N, 9.19. Found: C, 63.34; H, 5.72; N, 9.42.
17. 2O (0.15 g, 8.3 mmol) was added potassium carbonate (0.5 g, 3.6 mmol). The mixture was stirred at 100-110 °C for 2 h. The re-cooled mixture was diluted with an equal volume of ethyl acetate and filtered from Celite. The filtrate was evaporated under vacuum at below 50 °C to remove solvents. The residue was diluted with ethyl acetate and washed twice with water. The separated organic layer was dried and evaporated.
18. 4: C, 66.42; H, 6.62; N, 4.84. Found: C, 66.51; H, 6.78; N, 4.79.
19. 5: C, 65.74; H, 6.90. Found: C, 65.71; H, 6.82.