Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
α-Substituted Phosphonates. 43. Synthesis and Reactivity of 1,2,3,4-Tetrahydroisochinolin-1-phosphonatesN-Alkyl- and N-arylsubstituted 1,2,3,4-tetrahydroisochinolin-1-phosphonates 1 have been synthesized from the corresponding 3,4-dihydroisochinoliniumbromides 7 and triethyl-phosphite. The N-unsubstituted 1,2,3,4-tetrahydroisochinolin-1-phosphonate 10 is available starting from the 1,2,3,4-tetrahydroisochinolin-1-phosphonic acid by esterification with triethylformate and splitting off the formyl group of the primarily formed N-formyl derivative 14. - N-Quarternated tetrahydroisochinolines 19 and the 1-phosphorylated derivatives 17, respectively react with triethyl-phosphite in an unexpected way by dealkylation and not by splitting off the isochinolinring. - By Horner-synthesis with 1 the 1-aralkylidene-isochinolines 23 are available in moderate yields.
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