Synthesis of aryl-substituted piperidines by superacid activation of piperidones

被引：69

作者：

Klumpp, DA ^{[1
]}

Garza, M ^{[1
]}

Jones, A ^{[1
]}

Mendoza, S ^{[1
]}

机构：

[1] Calif State Polytech Univ Pomona, Dept Chem, Pomona, CA 91768 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 18期

关键词：

D O I：

10.1021/jo990454i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diarylpiperidines (8-12) may be prepared in good to excellent yields (80-99%) by the reaction of piperidones (3d-h) with benzene and the Bronsted superacid, trifluoromethanesulfonic acid (CF3SO3H, TfOH). Tropinone (6) and quinuclidone (7) also react in good yields with benzene in TfOH to give the condensation products (13 and 14). Ketal and acetal derivatives also give condensation products (8 and 24) upon reaction with C6H6 in TfOH. The conversion of 3g to 11 is sensitive to bath acid quantity and acid strength; a mechanism is proposed for the conversion that invokes dicationic intermediates.

引用

页码：6702 / 6705

页数：4

共 34 条

[1] COMPARISON OF THE EFFECTIVENESS OF SULFURIC-ACID AND TRIFLUORO-METHANESULFONIC ACID IN KOCH CARBOXYLATION REACTIONS [J].

BOOTH, BL ;

ELFEKKY, TA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (10) :2441-2446

[2] Using the electrostatic field effect to design a new class of inhibitors for cysteine proteases [J].

Conroy, JL ;

Sanders, TC ;

Seto, CT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4285-4291

[3] Superacid-catalyzed reductive Friedel-Crafts reaction of arenes using arenecarbaldehyde acetals [J].

Fukuzawa, S ;

Tsuchimoto, T ;

Hiyama, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :151-156

[4]

GIRINGAUZ A, 1997, MED CHEM, P169

[5]

Hofmann J. E., 1964, FRIEDEL CRAFTS RELAT, VII, P597

[6] Preparation of condensed aromatics by superacidic dehydrative cyclization of aryl pinacols and epoxides [J].

Klumpp, DA ;

Baek, DN ;

Prakash, GKS ;

Olah, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6666-6671

[7] Preparation of 3,3-diaryloxindoles by superacid-induced condensations of isatins and aromatics with a combinatorial approach [J].

Klumpp, DA ;

Yeung, KY ;

Prakash, GKS ;

Olah, GA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4481-4484

[8]

Klumpp DA, 1998, SYNLETT, P918

[9]

KLUMPP DA, 1991, J AM CHEM SOC, V113, P1364

[10] THE INTERACTIONS OF 1-ALKYL-4,4-DIPHENYLPIPERIDINES WITH OPIATE RECEPTORS [J].

NEUSER, D ;

STASCH, JP ;

WITTELER, M ;

KUHN, W ;

GERLACH, M ;

JUTZI, P ;

PRZUNTEK, H .

EUROPEAN JOURNAL OF PHARMACOLOGY, 1983, 87 (2-3) :315-318

← 1 2 3 4 →