Ritter reactions. XIII Reactivity of methyl Schiff bases with dimethyl acetylenedicarboxylate and mercaptoacetic acid

被引：7

作者：

Lin, QH ^{[1
]}

Djaidi, D ^{[1
]}

Bishop, R ^{[1
]}

Craig, DC ^{[1
]}

Scudder, ML ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1998年 / 51卷 / 09期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1071/C98025

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of several methyl imines with dimethyl acetylenedicarboxylate and with mercaptoacetic acid have been studied to investigate further the capricious behaviour of this functionality. The 1:1 adduct of imine (1) and dimethyl acetylenedicarboxylate is confirmed as the pyrroloisoquinoline structure (7) by X-ray methods [C17H17NO5, P (1) over bar, a 9.037(2), b 9.276(2), c 10.033(2) Angstrom, alpha 81.99(1), beta 81.28(1), gamma 64.99(2)degrees, Z 2, R 0.044]. New products from (2) and dimethyl acetylenedicarboxylate, the 1:1 adduct (10) which is readily converted into the known product (9), and the 1:2 adduct (12), are described. The structure of the last compound, which arises through a rearrangement process, was determined by X-ray crystallography [C27H36N2O9, Pca2(1), a 19.083(4), b 15.217(3), c 9.669(2) Angstrom, Z 4, R 0.038]. Methyl imines (1) and (4) undergo cyclocondensation with mercaptoacetic acid yielding thiazolidinone products but others are inert under similar conditions.

引用

页码：799 / 806

页数：8

共 28 条

[1] REACTIONS OF ACETYLENECARBOXYLIC ACIDS AND THEIR ESTERS WITH NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS
ACHESON, RM
[J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, 1963, 1 : 125 - 165
[2] ACHESON RM, 1978, ADV HETEROCYCL CHEM, V23, P263
[3] SIR92 - a program for automatic solution of crystal structures by direct methods
ALTOMARE, A
CASCARANO, G
GIACOVAZZO, G
GUAGLIARDI, A
BURLA, MC
POLIDORI, G
CAMALLI, M
[J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 : 435 - 435
[4] INTERACTION OF 1,2,3,4-TETRAHYDRO-4A-METHYL-4AH-CARBAZOLE WITH DIMETHYL ACETYLENEDICARBOXYLATE - A REEXAMINATION - CRYSTAL-STRUCTURES OF DIMETHYL 2A,3,4,5,5A,10-HEXAHYDRO-10-[(E)-1,2-BISMETHOXYCARBONYLVINYL]-5A-METHYLCYCLOBUTA[J]CARBAZOLE-1,2-DICARBOXYLATE AND DIMETHYL 1,2,3,3A,4,5,12B,12C-OCTAHYDRO-12C-METHOXY-4-METHOXYCARBONYLMETHYLENE-12B-METHYL-5-OXAZEPINO[3,2,1-JK]CARBAZOLE-6,7-DICARBOXYLATE
BARNWELL, N
MURPHY, CB
HOLGATE, SJW
MITCHELL, MB
LEONARD, GA
HUNTER, WN
JOULE, JA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (10): : 1855 - 1858
[5] RITTER REACTIONS .3. A SIMPLE ENTRY INTO THE 3-AZATRICYCLO[5.3.1.0/4,9]UNDECANE SYSTEM
BISHOP, R
HAWKINS, SC
IBANA, IC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) : 427 - 430
[6] Bishop R, 1991, COMPREHENSIVE ORGANI, P261
[7] RITTER REACTIONS .5. FURTHER INVESTIGATION OF THE 3-AZATRICYCLO[5.3.1.04,9]UNDEC-2-ENE SYSTEM
BONG, ICC
UNG, AT
CRAIG, DC
SCUDDER, ML
BISHOP, R
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (11) : 1929 - 1937
[8] BROSSI A, 1988, ORG SYNTH, V6, P1
[9] BUSING WR, 1962, ORFLS
[10] ABSORPTION CORRECTION IN CRYSTAL STRUCTURE ANALYSIS
DEMEULENAER, J
TOMPA, H
[J]. ACTA CRYSTALLOGRAPHICA, 1965, 19 : 1014 - +

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