Novel routes to indoles, indolines, quinolines and tetrahydroquinolines from N-(Cyclohexylidene)amines

Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms

“…Protected THIQs and 4,5,6,7-tetrahydro-1 H -indole were synthesized according to literature procedures. ( 26 )…”

1-Azaallylic Anions in Heterocyclic Chemistry

“…120 These bicyclic imines 406a-d could be further converted into indolines, tetrahydroindoles, quinolines, and tetrahydroquinolines. Treatment of bicyclic ketimines 406a and 406b with excess N-chlorosuccinimide in CCl 4 at room temperature afforded 3a,7,7-trichloro-3,3a,4,5,6,7-hexahydro-2H-indoles 408a and 408b.…”

Synthetic studies on the application of the intramolecular azide-alkene 1,3-dipolar cycloaddition reaction in the construction of the core structure of complex alkaloids

“…After screening different reaction conditions it was found that employing MeOH as solvent and heating for 3 hours at 140 ºC in a microwave reactor, the bicyclic imines 11-13 were detected in the 1 H-NMR M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 5 spectra of the crude reactions, but any attempt of purification resulted in very low yields or decomposition of the desired octahydroquinolines. This fact is probably due to the high propensity of piperideines to undergo spontaneous oxidation, [11] so we decided to transform compounds 11-13 directly into their corresponding nitrobenzoyl derivatives 14-16 through imine reduction with sodium borohydride and subsequent acylation of the resulting secondary amine with 3,5-dinitrobenzoyl chloride (3, in the presence of triethylamine.…”