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1,4‐Cycloaddition reactions. II. Preparation of p ‐dioxino[2,3‐ g ]furo[3,2‐ c ] quinolines, p ‐dioxino[2,3‐ f ] furo[3,2‐ c ] quinolines, and [1,3] dioxolo[4,5‐ g ] furo[3,2‐ c ] quinolines from 2,3‐dihydro‐5‐methylfuran and schiff bases
Author(s) -
Perricone S. C.,
Elslager Edward F.,
Worth Donald F.
Publication year - 1970
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570070119
Subject(s) - chemistry , quinoline , epimer , boron trifluoride , amine gas treating , medicinal chemistry , ethanol , stereochemistry , organic chemistry , catalysis
The boron trifluoride catalyzed 1,4‐addition of 2,3‐dihydro‐5‐methylfuran to N ‐( p ‐methoxy‐benzylidene)‐1,4‐benzodioxan‐6‐amine (II) gave 2 pairs of epimers, 2,3,3a,4,5,8,9,11b‐octahydro‐4‐( p ‐methoxyphenyl)‐11b‐methyl‐ p ‐dioxino[2,3‐ g ]furo[3,2‐ c ]quinoline (IIIa and b) and 2,3,7,8,8a,9.10,1la‐octahydro‐8‐( p ‐methoxyphenyl)‐11a‐methyl‐ p ‐dioxino[2,3‐ f ]furo[3,2‐ c ]quinoline (IVa and b). When N ‐( p ‐methoxybenzylidene)‐3,4‐methylenedioxyaniline (V) was condensed with 2,3‐dihydro‐5‐methylfuran in an analogous manner, a mixture of 2 epimers of 2,3,3a,4,5,10b‐hexahydro‐4‐( p ‐methoxyphenyl)‐10b‐methyl[1,3]dioxolo[4,5‐ g ]furo[3,2‐ c ]quinoline (VIa and b) was isolated. Treatment of this mixture with sulfur afforded 6‐( p ‐methoxyphenyl)‐8‐methyl‐1,3‐dioxolo[4,5‐ g ]quinoline‐7‐ethanol (VIII). Structural assignments for all of the products were made from NMR spectra. None of the compounds possessed appreciable biological activity.