Lewis acid-directed cyclocondensation of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine:: A new regioselective synthesis of oxygenated carbolines

被引：46
作者：
Engler, TA [1 ]
Wanner, J [1 ]
机构：
[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 08期
关键词：
D O I：
10.1021/jo9916176
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lewis acid-directed cyclocondensations of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine are reported. Benzofurans are obtained with BF3. OEt2 as a promoter, whereas use of excess amounts of TiCl4:Ti(OiPr)(4) leads to tetrahydrocarbolines. The latter reactions provide expedient routes to oxygen-substituted tetrahydrocarbolines and carbolines. As applications of this new methodology, the preparations of 1-[3-(dimethylamino)propyl] amino-7-methoxy- and 1-[3-(dimethylamino)propyl]amino-7,8-dimethoxy-5H-pyrido[4,3-b]indoles are described.
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页码：2444 / 2457
页数：14
相关论文
共 80 条
[21]   STEREOSPECIFIC LEWIS ACID-PROMOTED REACTIONS OF STYRENYL SYSTEMS WITH 2-ALKOXY-(6-ALKYL)-1,4-BENZOQUINONES - SCOPE, LIMITATIONS, AND SYNTHETIC APPLICATIONS [J].
ENGLER, TA ;
COMBRINK, KD ;
LETAVIC, MA ;
LYNCH, KO ;
RAY, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6567-6587
[22]   Contrasting reactivity in Lewis acid-promoted reactions of thio- and silyl-allenes with 1,4-benzoquinones [J].
Engler, TA ;
Agrios, K ;
Reddy, JP ;
Iyengar, R .
TETRAHEDRON LETTERS, 1996, 37 (03) :327-330
[23]   Lewis acid-directed reactions of benzoquinone mono-/bis-imines: Application to syntheses of substituted beta- and gamma-tetrahydrocarbolines [J].
Engler, TA ;
Wanner, J .
TETRAHEDRON LETTERS, 1997, 38 (35) :6135-6138
[24]   Lewis acid-directed reactions of quinones with styrenyl systems: The case of 2-methoxy-3-methyl-1,4-benzoquinone [J].
Engler, TA ;
Iyengar, R .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1929-1934
[25]   REGIOSELECTIVE LEWIS ACID-DIRECTED REACTIONS OF 2-ALKOXY-5-ALKYL-1,4-BENZOQUINONES WITH STYRENES - SYNTHESIS OF BURCHELLIN AND GUIANIN NEOLIGNANS [J].
ENGLER, TA ;
WEI, DD ;
LETAVIC, MA ;
COMBRINK, KD ;
REDDY, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6588-6599
[26]   Lewis acid-promoted reactions of styrenyl systems with benzoquinone bisimines: New regioselective syntheses of substituted 2-aryl-2,3-dihydroindoles and 2-arylindoles [J].
Engler, TA ;
Meduna, SP ;
LaTessa, KO ;
Chai, WY .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8598-8603
[27]   FORMATION AND ISOLATION OF ENANTIOMERICALLY PURE PRODUCTS IN QUANTITY FROM DIELS-ALDER REACTIONS OF 1,4-BENZOQUINONES [J].
ENGLER, TA ;
LETAVIC, MA ;
LYNCH, KO ;
TAKUSAGAWA, F .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) :1179-1183
[28]   CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA .
TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144
[29]  
FINLEY KT, 1988, CHEM QUINONOID COMPO, V2, P537
[30]  
Fleming I., 1989, ORG REACTIONS, V37, P57
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