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

[11] Ritter reactions .11. The diverse reactivity of 5,10-(azenometheno)-5H-dibenzo[a,d]cyclohepten-11-yl amides with dimethyl acetylenedicarboxylate
Djaidi, D
Bishop, R
Craig, DC
Scudder, ML
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (15): : 1859 - 1866
[12] DJAIDI D, 1995, J INCLUSION PHENOM, V20, P363
[13] ELZAHAR MI, 1994, PHARMAZIE, V49, P616
[14] GOVINDACHARI TR, 1984, HETEROCYCLES, V22, P585
[15] HRIB NJ, 1990, Patent No. 4933453
[16] Ibers J.A., 1974, INT TABLES XRAY CRYS, VIV
[17] JOHNSON CK, 1976, ORTEP 2
[18] Krimen L. I., 1969, ORG REACT, V17, P213, DOI DOI 10.1002/0471264180.0R017.03
[19] Lin QH, 1997, TETRAHEDRON, V53, P10899
[20] MAIN P, 1980, MULTAN80 SYSTEM COMP

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