Novel synthesis of benzo[c]quinolizinium salts and their condensed benzologs using α-oxoketene S,S-acetals

被引：0

作者：

Gupta, Akhilesh Kumar ^{[1
]}

机构：

[1] North Eastern Reg Inst Sci & Technol, Dept Chem, Nirjuli 791109, Itanagar, India

来源：

INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 2015年 / 54卷 / 08期

关键词：

Benzo[c] quinolizinium salts; tetrafluoroborates; alpha-oxoketene S; S-acetals; cycloaromatisation; quaternisation of nitrogen; COMPOSES ORGANIQUES SULFURES; POLARIZED KETENE DITHIOACETALS; BASE-CATALYZED REARRANGEMENTS; QUINOLIZINIUM SALTS; EPIBERBERINE; ACTIVATORS; ALKALOIDS; GUANIDINE; CARBONE; KETONES;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzo[c]quinolizinium tetrafluoroborates 9 have been synthesized in excellent yields by reacting a variety of alpha-oxoketene S,S-acetals 5 derived from a variety of cyclic and acyclic active methylene ketones, with 2-methylquinolyllithium and 2,4-dimethyl-6-methoxyquinolyllithium followed by cycloaromatisation of the resulting carbinol acetals 7 in the presence of borontrifluoride etherate in refluxing benzene.

引用

页码：972 / 978

页数：7

共 49 条

[1] Competitive intramolecular nucleophilic aromatic substitution: A new route to coumarins [J].

Alonso, C ;

Olmstead, MM ;

Nantz, MH ;

Kurth, MJ .

CHEMICAL COMMUNICATIONS, 2001, (07) :639-640

[2]

[Anonymous], 1978, HDB PRACTICAL ORGANI, P913

[3] POLARIZED KETENE DITHIOACETALS .32. STUDIES ON BASE-CATALYZED REARRANGEMENTS OF 2-BIS(METHYLTHIO)METHYLENEINDAN-1-ONE, 2-BIS(METHYLTHIO)METHYLENE-1-TETRALONE, AND 3-BIS(METHYLTHIO)METHYLENE-2,3-DIHYDRO-1-BENZOTHIOPYRAN-4-ONE [J].

APPARAO, S ;

DATTA, A ;

ILA, H ;

JUNJAPPA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :921-924

[4] POLARIZED KETENE DITHIOACETALS .41. STUDIES ON BASE-CATALYZED REARRANGEMENTS OF 1,1-BIS(ALKYLTHIO)-2-AROYLPENTA-1,4-DIENES TO NOVEL 1,5-BIS(ALKYLTHIO)-2-AROYLPENTA-1,3-DIENES VIA A 1,5-ALKYLTHIO SHIFT [J].

APPARAO, S ;

BHATTACHARJEE, SS ;

ILA, H ;

JUNJAPPA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (03) :641-645

[5] POLYCYCLIC AROMATIC NITROGEN CATIONS [J].

ARAI, S ;

HIDA, M .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1992, 55 :261-358

[6] Synthesis of polycyclic azonia-aromatic compounds by photo-induced intramolecular quaternization:: Azonia derivatives of benzo[c]phenanthrene, [5]helicene and [6]helicene [J].

Arai, S ;

Ishikura, M ;

Yamagishi, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (09) :1561-1567

[7] SYNTHESIS AND REACTIONS OF METHYLBENZO[C]QUINOLIZINIUM SALTS [J].

ARAI, S ;

ARAI, H ;

TABUCHI, K ;

YAMAGISHI, T ;

HIDA, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (01) :215-220

[8]

Arai S, 1992, CHEMINFORM ABSTRACT, V23

[9]

ASOKAN CV, 1985, SYNTHESIS-STUTTGART, P163

[10] CYCLOAROMATIZATION OF ALPHA-OXOKETENE DITHIOACETALS WITH 2-PICOLYLLITHIUM - A FACILE QUINOLIZINIUM CATION ANNELATION .58. [J].

BALU, MP ;

ILA, H ;

JUNJAPPA, H .

TETRAHEDRON LETTERS, 1987, 28 (26) :3023-3026

← 1 2 3 4 5 →