Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines
A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp3)-C(sp2) and C(sp 2)-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp3C-H/sp2C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.
1-alkyl-1,4-dihydro-4-imino-3-quinolinecarboxylates. Part 1. General synthesis
The synthesis of the hitherto unreported 1-alkyl-1,4-dihydro-4-(ethylimino or arylimino)-3-quinoline-carboxylates is described. The method utilises a 2-halogeno-benzenecarboximidoyl chloride for C-imidoylation of an ethyl 3-alkylamino-2-butenoate or 2-pro
Staskun, Benjamin,Van Es, Theodorus
p. 92 - 99
(2007/10/03)
PROTOTROPIC MIGRATIONS IN THE PHOSPHORYLATION OF IMIDOYL CHLORIDES CONTAINING HYDROGEN ON THE N-α-CARBON ATOM. III. PHOSPHORYLATION OF SUBSTITUTED N-BENZYLBENZIMIDOYL CHLORIDES WITH TRIETHYL PHOSPHITE
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Onys'ko, P. P.,Kim, T. V.,Kiseleva, E. I.,Sinitsa, A. D.
p. 1104 - 1110
(2007/10/02)
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