2019
DOI: 10.1021/acs.orglett.8b03935
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Synthesis of 1-Amino-2H-quinolizin-2-one Scaffolds by Tandem Silver Catalysis

Abstract: An efficient tandem cycloisomerization–amination reaction catalyzed by silver is described. This rapid and atom-economic reaction delivered 1-amino-2H-quinolizin-2-one scaffolds in high yields under mild conditions. The reaction could be extended to an asymmetric version albeit with moderate enantioselective excess of the products. In addition, the products can be easily reduced into various azabicycles containing 4-pyridones, which are important building blocks in organic synthesis.

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Cited by 14 publications
(6 citation statements)
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“…[1,2] [CAS:1340531-00-1], 5h [CAS: 93139-50-5] were prepared according to a literature procedure. [3,4]…”
Section: Methodsmentioning
confidence: 99%
“…[1,2] [CAS:1340531-00-1], 5h [CAS: 93139-50-5] were prepared according to a literature procedure. [3,4]…”
Section: Methodsmentioning
confidence: 99%
“…[1,2] Alkyne 5b [CAS:7515- [CAS:1340531-00-1], 5h [CAS: 93139-50-5] were prepared according to a literature procedure. [3,4] III. Synthesis of Acyl Fluorides 2-Iodobenzoic acid (1.24 g, 5.0 mmol) and CH 2 Cl 2 (15 mL) were added to a 100 mL two-necked flask.…”
Section: Methodsmentioning
confidence: 99%
“…Asymmetric study on axial chirality resulted in 59 % ee . The plausible mechanism can be explained by two competitive pathways, initial α‐keto amination followed by π‐activated cyclization or initial cyclization followed by C−H amination [32] …”
Section: Metamorphosis Of Heteroarene‐tethered αβ‐Ynonesmentioning
confidence: 99%
“…The plausible mechanism can be explained by two competitive pathways, initial a-keto amination followed by p-activated cyclization or initial cyclizationfollowed by CÀHa mination. [32] 3.3. Metamorphosis involving cycloaddition reactions Multi-substituted azafluorenones,i ndenothiophenones, and benzo [b]furanones 111 were synthesized via solventf ree, Ru catalyzed [2+ +2+ +2] cycloaddition of carbonyl bridged a,wdiynes 109 and alkynes 110.5mol %R uCl 3 Cn H 2 Oi nt he absence of any solventa nd heating at 50-80 8Cf ound to be best condition for this transformation.A long with aw ide range of substrate scope, solvent free reaction condition and use of stable Ru-catalyst withouta ny ligand are the major highlights (Scheme 22).…”
Section: Metamorphosis Involving Cycloisomerizationand Annulation Reamentioning
confidence: 99%