REACTION OF BENZOCYCLOBUTENOXIDES WITH NITRILES - SYNTHESIS OF HYPECUMINE AND OTHER 3-SUBSTITUTED ISOQUINOLINES

被引：28

作者：

FITZGERALD, JJ ^{[1
]}

MICHAEL, FE ^{[1
]}

OLOFSON, RA ^{[1
]}

机构：

[1] PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 49期

关键词：

D O I：

10.1016/0040-4039(94)88462-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of benzocyclobuten-2-ols with MeLi affords o-tolualdehyde anions which in the presence of nitriles cyclize to 3-substituted isoquinolines. Examples include the synthesis of the alkaloid hypecumine from the precursors, 14 and 19 (1:1), in 50% yield.

引用

收藏

页码：9191 / 9194

页数：4

相关论文

共 16 条

[1]

CAROTTI A, 1979, SYNTHESIS-STUTTGART, P56

[2] APPLICATIONS OF SODAMIDE-CONTAINING COMPLEX BASES IN ORGANIC SYNTHESIS [J].

CAUBERE, P .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (09) :301-308

[3] CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS . 28 . ALPHA-BROMO DERIVATIVES OF BENZOCYCLOBUTENONE [J].

CAVA, MP ;

MUTH, K ;

MANGOLD, D .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10) :2947-&

[4] DIELS-ALDER REACTIONS OF ALPHA-OXY-ORTHO-XYLYLENES [J].

CHOY, W ;

YANG, HL .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5796-5798

[5]

DYALL LK, 1975, J CHEM SOC P1, P1

[6]

FARGE D, 1980, Patent No. 4189480

[7]

FARGE D, 1981, Patent No. 4261992

[8] REACTION OF BENZOCYCLOBUTENOXIDES WITH ALDEHYDES - SYNTHESIS OF PESHAWARINE AND OTHER 3,4-DIHYDROISOCOUMARINS [J].

FITZGERALD, JJ ;

PAGANO, AR ;

SAKODA, VM ;

OLOFSON, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4117-4121

[9] A RAPID, CONVERGENT, AND REGIOSELECTIVE SYNTHESIS OF ANTHRACENES [J].

FITZGERALD, JJ ;

DRYSDALE, NE ;

OLOFSON, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7122-7126

[10] A FACILE TOTAL SYNTHESIS OF (+/-)-CHERYLLINE VIA AN AZIRIDINIUM INTERMEDIATE [J].

KAMETANI, T ;

HIGASHIYAMA, K ;

HONDA, T ;

OTOMASU, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (12) :2935-2937