FUNCTIONALIZATION OF THE ALKOXY GROUP OF ALKYL ARYL ETHERS - DEMETHYLATION, ALKYLTHIOLATION AND REDUCTION OF 5-METHOXYINDOLES

被引：9

作者：

CAUBERE, C

CAUBERE, P

RENARD, P

BIZOTESPIART, JG

IANELLI, S

NARDELLI, M

JAMARTGREGOIRE, B

机构：

[1] ADIR,F-92415 COURBEVOIE,FRANCE

[2] UNIV PARMA,IST CHIM GEN,CNR,CTR STRUTTURIST DIFFRATTOMETRICA,I-43100 PARMA,ITALY

来源：

TETRAHEDRON | 1994年 / 50卷 / 47期

关键词：

D O I：

10.1016/S0040-4020(01)89350-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of AlX(3)-RSH three kinds of reactions may take place with 5-methoxy indoles : demethylation, alkylthiolation and reduction. The two latter reactions have never been observed to the present, with such reagents. Considerable improvement in the selective demethylation was found when PhCH(2)SH replaced EtSH previously used in such transformations. Factors leading to selective alkylthiolations or reductions are shown and mechanisms are proposed to explain these new reactions.

引用

页码：13433 / 13448

页数：16

共 14 条

[1] ALCL3-N,N-DIMETHYLANILINE - A NOVEL BENZYL AND ALLYL ETHER CLEAVAGE REAGENT [J].

AKIYAMA, T ;

HIROFUJI, H ;

OZAKI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (07) :1932-1938

[2]

BHATT MV, 1982, SYNTHESIS-STUTTGART, P249

[3] COMPLEX BASES PROMOTED ARYNIC CYCLIZATIONS OF HALOGENATED IMINES OR ENAMINES - A REGIOCHEMICAL SYNTHESIS OF INDOLE-DERIVATIVES [J].

CAUBERE, C ;

CAUBERE, P ;

RENARD, P ;

BIZOTESPIART, JG ;

JAMARTGREGOIRE, B .

TETRAHEDRON LETTERS, 1993, 34 (43) :6889-6892

[4]

CAUBERE C, IN PRESS SYNTH COMMU

[5]

DOASEE M, 1987, J AM CHEM SOC, V109, P3098

[6] SUBSTITUTED THIOPYRANO[2,3,4-C,D]INDOLES AS POTENT, SELECTIVE, AND ORALLY-ACTIVE INHIBITORS OF 5-LIPOXYGENASE - SYNTHESIS AND BIOLOGICAL EVALUATION OF L-691,816 [J].

HUTCHINSON, JH ;

RIENDEAU, D ;

BRIDEAU, C ;

CHAN, C ;

DELORME, D ;

DENIS, D ;

FALGUEYRET, JP ;

FORTIN, R ;

GUAY, J ;

HAMEL, P ;

JONES, TR ;

MACDONALD, D ;

MCFARLANE, CS ;

PIECHUTA, H ;

SCHEIGETZ, J ;

TAGARI, P ;

THERIEN, M ;

GIRARD, Y .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (19) :2771-2787

[7]

IANELLI S, 1994, IN PRESS ACTA CRYS C, V50

[8]

MCOWIE JPW, ORGANIC SYNTHESES CO, P412

[9]

NIWA H, 1981, TETRAHEDRON LETT, V22, P4229

[10]

NODA M, 1980, J ORG CHEM, V45, P4275

← 1 2 →