A novel substitution reaction of tetrahydropyrano[3,4-b]indole derivative - Chain extension and structural correlation study

Heterocycles

Volumn 60, Issue 5, 2003, Pages 1095-1110

  Chou, Shan Yen ^a  

^a DEVELOPMENT CENTER FOR BIOTECHNOLOGY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1 CHLOROMETHYLTETRAHYDROPYRANO[3,4 B]INDOLE 1 ACETIC ACID ESTER DERIVATIVE; ACETIC ACID ESTER; INDOLEACETIC ACID DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; CYANATION; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0038710861     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-9703     Document Type: Article

References (10)

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7. Compound (2) has been determined by a 2 D NMR spectrum and correlation studies, see: S-Y. Chou, C-L. Tseng, and S-F. Chen, Heterocycles, 1999, 51, 1527.
8. A related skeletal rearrangement of a benzazepine skeleton, in which a tertiary amine acts as the nucleophilic center has been reported, see: H. Irie, S. Tani and H. Yamane. J. Chem. Soc., Perkin Trans. 1, 1972, 2986.
9. The corresponding α- and β-methylene protons of the alcohol (20) and the bromide (21) also reveal comparable chemical shifts (see EXPERIMENTAL). The corresponding ring expansion skeleton would not show comparable signals.
10. Phenyl-substituted tryptophols are prepared by refluxing the corresponding phenylhydrazines and 2-ethoxytetrahydrofuran in 95% ethanol, this process, is a modification of one in the literature, wherein 2-ethoxytetrahydrofuran is employed as the substitute for the highly acid-sensitive 2,3-dihydrofuran, see: B. Mckittrick, A. Failli, R. J. Steffan, R. M. Soll, P. Hughes, J. Schmid, A. A. Asselin, C. C. Shaw, R. Noureldin, and G. Gavin, J. Heterocycl. Chem., 1990, 27, 2151.