A New Heterocycle Synthesis: Pyrroles and Quinolines

Oxidation of enamine-esters with lead tetra-acetate. Part 1. Products from some N-alkylaminofumarates

“…spectrum, if another broad doublet absorption ( T 5.58) is identified as that of the aminomaleate NH group; this is at higher field than that ( T 4.25) of compound (2b), but very close to that ( 7 5.60) of the corresponding NH group in compound (5a).11 Doubleresonance experiments demonstrated convincingly that the two N H doublets were not a mutually coupled AB system, but that they were independently coupled t o N-CH groups responsible for the broad resonance at z 7.0. We are unable to explain why (13) should be preferred to a bis-fumarate structure, in view of the preference for the latter configuration shown by the enamines (1) .13 A series of oxidative dimers (10; a-c and e) was obtained from the corresponding enamines (lc, f, g, and e) by treatment with LTA. 1.r.…”

Synthesis of Acridines by the [4 + 2] Annulation of Arynes and 2-Aminoaryl Ketones

“…The reaction of ortho -aminoaryl carbonyl compounds and alkynes containing electron-withdrawing groups is a process analogous to our aryne methodology 31. First reported in the 1960’s, this chemistry affords good yields of the corresponding 2,3,4-trisubstituted quinolines in one step (eq.…”

Synthesis of fluorine-containing quinoline-2,3-dicarboxylates from products of vicarious nucleophilic substitution of hydrogen in 3-fluoronitroarenes

“…13 Methods for the synthesis of quinoline 2,3 dicarboxy late derivatives by the reactions of ortho nitroarenealde hydes with diethyl (diethoxyphosphinyl)succinate 14 and by the condensation of ortho aminoarenecarbaldehydes * Dedicated to Academician A. I. Konovalov on his 75th birthday. with diethyl oxaloacetate 15 or acetylenedicarboxylates 16 are of limited use, because the starting substrates are diffi cultly accessible; moreover, aminoaldehydes are unstable.…”