SYNTHETIC STUDIES ON INDOLES AND RELATED-COMPOUNDS .26. THE DEBENZYLATION OF PROTECTED INDOLE NITROGEN WITH ALUMINUM-CHLORIDE .2.

被引：0

作者：

WATANABE, T ^{[1
]}

KOBAYASHI, A ^{[1
]}

NISHIURA, M ^{[1
]}

TAKAHASHI, H ^{[1
]}

USUI, T ^{[1
]}

KAMIYAMA, I ^{[1
]}

MOCHIZUKI, N ^{[1
]}

NORITAKE, K ^{[1
]}

YOKOYAMA, Y ^{[1
]}

MURAKAMI, Y ^{[1
]}

机构：

[1] TOHO UNIV, SCH PHARMACEUT SCI, 2-2-1 MIYAMA, FUNABASHI, CHIBA 274, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1991年 / 39卷 / 05期

关键词：

DEBENZYLATION; ALUMINUM CHLORIDE; INDOLE; BENZAMIDE; BENZENE; ANISOLE;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new debenzylation method using aluminum chloride in benzene or anisole, which had been developed by us for N-benzyl-2-acyl- and -2-ethoxycarbonylindoles, was applied to benzyl derivatives of other types of indoles and related compounds. Among them, N-benzyl derivatives of fully aromatized indoles, carbazoles and beta-carbolines, and some benzamides were debenzylated successfully, whereas those of oxindoles and heterocyclic amides were not. As to the effect of a p-substituent on the benzyl group, it was found that an electron-donating substituent accelerates deprotection, whereas an electron-attracting substituent delays or prevents deprotection.

引用

页码：1152 / 1156

页数：5

共 50 条

[31] SYNTHETIC STUDIES ON LYCORICIDINE AND RELATED COMPOUNDS .2. TOTAL SYNTHESIS OF (+ OR -)-LYCORICIDINE
OHTA, S
KIMOTO, S
CHEMICAL & PHARMACEUTICAL BULLETIN, 1976, 24 (12) : 2977 - 2984
[32] SYNTHETIC STUDIES OF INDOLES AND RELATED-COMPOUNDS .17. THE FRIEDEL-CRAFTS ACYLATION OF ETHYL PYRROLE-2-CARBOXYLATE - SCOPE, LIMITATIONS, AND APPLICATION TO SYNTHESIS OF 7-SUBSTITUTED INDOLES
MURAKAMI, Y
TANI, M
ARIYASU, T
NISHIYAMA, C
WATANABE, T
YOKOYAMA, Y
HETEROCYCLES, 1988, 27 (08) : 1855 - 1860
[33] SYNTHETIC STUDIES ON INDOLES AND RELATED-COMPOUNDS .30. A NEW GENERAL SYNTHETIC ROUTE FOR 1-SUBSTITUTED 4-OXYGENATED BETA-CARBOLINES
SUZUKI, H
YOKOYAMA, Y
MIYAGI, C
MURAKAMI, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (08) : 2170 - 2172
[34] SYNTHETIC STUDIES OF INDOLES AND RELATED-COMPOUNDS .18. REGIOSELECTIVITY IN THE VILSMEIER-HAACK REACTION OF N-BENZYL-1,2,3,4-TETRAHYDROCARBAZOLE
MURAKAMI, Y
YOKOYAMA, Y
MIURA, T
NOZAWA, S
TAKEDA, E
SUZUKI, H
HETEROCYCLES, 1988, 27 (10) : 2341 - 2344
[35] SYNTHETIC OXYTOCICS .2. PHARMACOLOGY OF 3-(PIPERIDYL-(N)-METHYL)-INDOLES AND RELATED COMPOUNDS
DEJONGH, DK
VANPROOSDIJHARTZEMA, EG
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 1952, 105 (02): : 130 - 138
[36] STUDIES ON GASTRIC ANTIULCER ACTIVE AGENTS .2. SYNTHESIS OF TETRAZOLE ALKANAMIDES AND RELATED-COMPOUNDS
UCHIDA, M
KOMATSU, M
MORITA, S
KANBE, T
NAKAGAWA, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (02) : 322 - 326
[37] STUDIES ON CONDENSED TRIAZINES AS CHEMOTHERAPEUTIC-AGENTS .2. SYNTHESIS OF 1,2,4-TRIAZINO[5,6-B]INDOLES AND RELATED-COMPOUNDS
RAM, VJ
ARCHIV DER PHARMAZIE, 1980, 313 (02) : 108 - 113
[38] QUANTITATIVE STRUCTURE ACTIVITY STUDIES OF PYRETHROIDS .26. RATES OF DEVELOPMENT OF KNOCKDOWN AND DEPOLARIZING EFFECTS INDUCED BY KADETHRIC ACID-ESTERS AND RELATED-COMPOUNDS
MATSUDA, K
NAKAMURA, H
HAMADA, M
NISHIMURA, K
FUJITA, T
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 1991, 41 (02) : 178 - 189
[39] STUDIES ON ANTIALLERGY AGENT .2. SYNTHESIS OF 3-BENZOYLACRYLIC ACIDS AND THE RELATED-COMPOUNDS
OZEKI, K
ISHIZUKA, Y
SAWADA, M
SHIMAMURA, H
ICHIKAWA, T
SATO, M
YAGINUMA, H
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1987, 107 (04): : 268 - 273
[40] STUDIES OF ORGANOMOLYBDENUM COMPOUNDS .2. SYNTHESIS, STRUCTURE, AND PROPERTIES OF DIOXODINEOPENTYL(2,2'-BIPYRIDYL)MOLYBDENUM(VI) AND OF RELATED-COMPOUNDS
SCHRAUZER, GN
HUGHES, LA
STRAMPACH, N
ROSS, F
ROSS, D
SCHLEMPER, EO
ORGANOMETALLICS, 1983, 2 (04) : 481 - 485

← 1 2 3 4 5 →