Isoquinolines from indenes

There are two syntheses of isoquinolines from indenes by oxidation and subsequent addition of ammonia or ammonium salts, differing only in oxidizing medium. Both are summarized in equation (76) in the first, ozonolysis with a reductive work-up is used (80JOC5312), in the second, periodate and catalytic amounts of osmium tetroxide (81JOC4999). The yields can be very good. 

Isoquinolines. A one-pot synthesis of isoquinolines from indenes involves ozonation followed by treatment of the intermediate with ammonia (equation 1).1... 

The Analysis of Total Reaction Paths According to the above analysis of each path, it can be concluded that the most feasible formation processes of PI (CgHe, HC = C—C=N) and P2 (CeHsC N, HCsCH) during quinoline and isoquinoline pyrolysis should involve two parts leading to the intermediate 1-indene imine with two conformational tautomers and yielding PI and P2 from the common intermediate. 

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