Abnormal products in the Bischler-Napieralski isoquinoline synthesis

被引：36

作者：

Doi, S ^{[1
]}

Shirai, N ^{[1
]}

Sato, Y ^{[1
]}

机构：

[1] NAGOYA CITY UNIV,FAC PHARMACEUT SCI,MIZUHO KU,NAGOYA,AICHI 467,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 15期

关键词：

D O I：

10.1039/a701332i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of N-[2-(4-methoxyphenyl)ethyl]benzamides with phosphorus pentoxide (and phosphoryl chloride) gives 7-methoxy-1-phenyl-3,4-dihydroisoquinolines (a normal Bischler-Napieralski reaction product) and 6-methoxy-1-phenyl-3,4-dihydroisoquinoli (an abnormal reaction product), The reaction mechanism is discussed.

引用

页码：2217 / 2221

页数：5

共 11 条

[1] AHLNWALIA GS, 1931, J CHEM SOC, P2057
[2] ON THE STEREOCHEMISTRY OF THE PICTET-SPENGLER REACTION
BAILEY, PD
[J]. TETRAHEDRON LETTERS, 1987, 28 (43) : 5181 - 5184
[3] ERIGUCHI A, 1982, CHEM PHARM BULL, V30, P428
[4] CORRELATION OF THE VONBRAUN, RITTER, BISCHLER-NAPIERALSKI, BECKMANN AND SCHMIDT REACTIONS VIA NITRILIUM SALT INTERMEDIATES
FODOR, G
NAGUBANDI, S
[J]. TETRAHEDRON, 1980, 36 (10) : 1279 - 1300
[5] SYNTHESIS OF 9-PHENYL-H-5-2-BENZAZEPINES BY RING EXPANSION OF 1-PHENYL-2,3-DIHYDROISOQUINOLINES
LANTOS, I
BHATTACHARJEE, D
EGGLESTON, DS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) : 4147 - 4150
[6] SYNTHESIS AND MOLECULAR MODELING OF 1-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINES AND RELATED 5,6,8,9-TETRAHYDRO-13BH-DIBENZO[A,H]QUINOLIZINES AS D-1 DOPAMINE ANTAGONISTS
MINOR, DL
WYRICK, SD
CHARIFSON, PS
WATTS, VJ
NICHOLS, DE
MAILMAN, RB
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (25) : 4317 - 4328
[7] MUNDY BP, 1988, NAME REACTIONS REAGE, P32
[8] OPTIMIZATION OF PARAMETERS FOR SEMIEMPIRICAL METHODS .1. METHOD
STEWART, JJP
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1989, 10 (02) : 209 - 220
[9] STEWART JJP, 1995, JCPE NEWSLETTER, V6, P76
[10] SUGAWARA J, 1935, YAKUGAKU ZASSHI, V55, P224

← 1 2 →