Reisert compounds

The Reisert compound 93, prepared from quinoline derivatives 92, gave upon reaction with dimethyl acetylenedicarboxylate the pyrroloquinoline 95. Reduction of 93 gave the tetrahydro derivative that upon reaction with dimethyl acetylenedicarboxylate afforded 96 (85JOC722). Reaction of 94 with acrylonitrile in presence of base gave pyrroloquinoline 97 (77JCS(P1)2018) (Scheme 18). 

Bromocyclocarbamation reaction of l-allyl-2-[( R)-menthyloxycarbo-nyl] derivatives of Reisert compounds 102 was accompanied by BrOMe addition to the C(3)-C(4) double bond to give 2-bromo-methyl-[l,3]oxazino[4,3-a]isoquinoline-4-ones 103 either under condition A with Br2 or under condition B using pyridinium tribromides (08JHC1651). 

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