147808-86-4Relevant articles and documents
The Intramolecular 1,3-Dipolar Cyclisation of Mesoionic Species Generated by the Thermolysis of the Mixed Anhydrides of Acetic and N-Alkynoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acids
Sainsbury, Malcolm,Strange, Rosalind H.,Woodward, Peter R.,Barsanti, Paul A.
, p. 2065 - 2076 (1993)
The intramolecular cyclisations of mesoionic intermediates formed by heating N-alkynoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids C-(CH2)nCO, where n = 3 or 4> with acetic anhydride, have been investigated.The final products are octahydropentalenoisoquinolines and hexahydroindenoisoquinolines, respectively, formed by the expulsion of carbon dioxide from the initial adducts.The behaviour of alkenes and alkynes as dienophiles in intermolecular versions of the cycloaddition reactions have also been studied.Alkynes bearing electron withdrawing groups afford pyrroloisoquinolines, but unless alkenes, such as benzylidenemalonodinitrile are used (where the first formed adduct can eliminate HCN, prior to loss of CO2), the reactions fail.