OXIDATIVE FUNCTIONALIZATION OF SOME ASPIDOSPERMA ALKALOIDS WITH TRIFLUOROACETIC-ANHYDRIDE

被引：11

作者：

LEVY, J

SOUFYANE, M

MIRAND, C

DEMAINDREVILLE, MD

ROYER, D

机构：

[1] Laboratoire de Transformations et Synthèse de Substances Naturelles, associé au CNRS, Université de Reims Champagne-Ardenne, F51096 Reims Cedex, 51, rue Cognacq- Jay

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(00)93433-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

When reacted with trifluoroacetic anhydride (TFAA) in pyridine at room temperature, tabersonine 1 and its derivatives 2, 3 suffered oxidation of the tertiary amine resulting in the formation of enaminotrifluoroketones 7, 9 and 10, respectively. A precedent to such a reaction exists in literature 11.

引用

页码：5081 / 5084

页数：4

共 10 条

[1] MODIFICATION DE LA REACTION DE POLONOVSKI ACTION DE LANHYDRIDE TRIFLUOROACETIQUE SUR UN AMINOXYDE [J].

CAVE, A ;

KANFAN, C ;

POTIER, P ;

LEMEN, J .

TETRAHEDRON, 1967, 23 (12) :4681-&

[2]

DEMAINDREVILLE D, 1981, B SOC CHIM FR, P179

[3]

DJERASSI C, 1962, TETRAHEDRON LETT, P235

[4]

LARONZE JY, 1988, SYNTHESIS-STUTTGART, P619

[5]

LEMEN J, 1965, EXPERIENTIA, V21, P508

[6] THE HOFMANN-LIKE FRAGMENTATION INDUCED BY N-ACYLATION OF 1-METHYL-1-AZA-4-CYCLANONES AND ITS USE IN THE SYNTHESIS OF 2-AZA-HYDRINDANONES AND 2-AZA-DECALONES [J].

LEVY, J ;

LARONZE, JY ;

JANOSSAPI .

TETRAHEDRON LETTERS, 1988, 29 (27) :3303-3306

[7]

PLAT M, 1962, TETRAHEDRON LETT, P271

[8]

PLAT M, 1962, B SOC CHIM FR, P1082

[9] HYDROGEN TRANSFER FROM TERTIARY-AMINES TO TRIFLUOROACETIC-ANHYDRIDE [J].

SCHREIBER, SL .

TETRAHEDRON LETTERS, 1980, 21 (11) :1027-1030

[10] REACTIONS OF ENAMINES WITH TRIFLUOROACETIC-ANHYDRIDE - TRIFLUOROACETYLATION AND THE FORMATION OF 1.3-OXAZINES [J].

VERBOOM, W ;

REINHOUDT, DN ;

HARKEMA, S ;

VANHUMMEL, GJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (17) :3339-3342

← 1 →