
%0 Journal Article
%A Lin, Qinghong 
%A Djaidi, Djamal 
%A Bishop, Roger 
%A Craig, Donald C. 
%A Scudder, Marcia L. 
%T Ritter Reactions. XIII  Reactivity of Methyl Schiff Bases with Dimethyl Acetylenedicarboxylate and Mercaptoacetic Acid
%J Australian Journal of Chemistry
%D 1998/10/05
%V 51
%N 9
%P 799-806
%K 
%R https://doi.org/10.1071/C98025
%U https://www.publish.csiro.au/paper/C98025 
%X 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 &#91;C17H17NO5, P -1, a 9&#183;037(2), b 9&#183;276(2), c 10&#183;033(2) &#197;, &#945; 81&#183;99(1), &#946; 81&#183;28(1), &#947; 64&#183;9(2)&#176;, Z 2, R 0&#183;044&#93;. 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 &#91;C27H36N2O9,P ca21, a 19&#183; 083(4), b 15&#183;217(3), c 9&#183;669(2) &#197;, Z 4, R 0&#183;038&#93;. Methyl imines (1) and (4) undergo cyclocondensation with mercaptoacetic acid yielding thiazolidinone products but others are inert under similar conditions. 
