2017
DOI: 10.1016/j.tetlet.2017.04.036
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A facile and versatile protocol for the one-pot PhI(OAc) 2 mediated divergent synthesis of quinazolines from 2-aminobenzylamine

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Cited by 38 publications
(18 citation statements)
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“…8 Despite these signicant advances, the most classical and general approaches for the synthesis of quinazolines and quinazolinones still strongly rely on the condensation between o-aminobenzylamines and aldehydes followed by the oxidation of the resulting aminal intermediates in the laboratory and industry. However, this protocol generally requires the use of a large excess of toxic oxidants, such as DDQ, 9 MnO 2 , 10 PhI(OAc) 2 , 11 and NaClO, 12 or homogeneous transition metal complexes ligated with well-dened ligands, 8d,13 which signicantly limit its practical application, especially for pharmaceutical synthesis. Therefore, the development of efficient, stable and cost-effective heterogeneous non-precious metal catalysts for accessing quinazolines and quinazolinones is highly desirable.…”
Section: Introductionmentioning
confidence: 99%
“…8 Despite these signicant advances, the most classical and general approaches for the synthesis of quinazolines and quinazolinones still strongly rely on the condensation between o-aminobenzylamines and aldehydes followed by the oxidation of the resulting aminal intermediates in the laboratory and industry. However, this protocol generally requires the use of a large excess of toxic oxidants, such as DDQ, 9 MnO 2 , 10 PhI(OAc) 2 , 11 and NaClO, 12 or homogeneous transition metal complexes ligated with well-dened ligands, 8d,13 which signicantly limit its practical application, especially for pharmaceutical synthesis. Therefore, the development of efficient, stable and cost-effective heterogeneous non-precious metal catalysts for accessing quinazolines and quinazolinones is highly desirable.…”
Section: Introductionmentioning
confidence: 99%
“…For the reduction voltammograms, 0.1 m tetra‐ n ‐butylammonium hexafluorophosphate (TBAPF 6 ) in MeCN was used as the supporting electrolyte. 2,3‐Di‐ p ‐tolylbenzo[ g ]quinoxaline (mpqx), 2,3‐bis(4‐methoxyphenyl)benzo[ g ]quinoxaline (mopqx), and 2‐(quinolin‐2‐yl)quinazoline (qqz) were synthesized following procedures reported in the literature . Cyclometalated iridium dichloro‐bridged dimers with the general formula [(C^N) 2 Ir(μ‐Cl) 2 Ir(C^N) 2 ] were prepared according to procedures reported in the literature .…”
Section: Methodsmentioning
confidence: 99%
“…2,3-Di-p-tolylbenzo[g]quinoxaline (mpqx), 2,3-bis(4-methoxyphenyl)benzo[g]quinoxaline (mopqx), and 2-(quinolin-2-yl)quinazoline (qqz) were synthesized following procedures reported in the literature. [13,14] Cyclometalated iridium dichloro-bridged dimers with the general formula [(C^N) 2 Ir(m-Cl) 2 Ir(C^N) 2 ]w ere prepared according to procedures reported in the literature. [15] All experiments involving IrCl 3 ·3H 2 Oo ra ny other iridium species were carried out in an inert atmosphere.…”
Section: Experimental Section Generali Nformationmentioning
confidence: 99%
“…Oxidative condensation of 2-aminobenzylamines with aldehydes is an attractive strategy to construct the pyrimidine ring. 25 K 2 S 2 O 8 is a mild oxidant, which has been utilized in oxidative coupling reactions to construct nitrogen containing heterocycles. [26][27][28][29] Herein, we report K 2 S 2 O 8mediated aerobic oxidative coupling of 6-amino-7-(aminomethyl)-thiazolino-2-pyridones with aldehydes for the synthesis of a novel tricyclic pyrimidine fused 2-pyridone scaffold.…”
Section: Introductionmentioning
confidence: 99%