Production Method 1

87-13-8

109-06-8

88612-71-9

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  -78 °C; 10 min, -78 °C; 30 min, -78 °C
1.2 Solvents: Tetrahydrofuran ;  -78 °C; 4 h, -78 °C; -78 °C → 0 °C; 3 h, 0 °C

Reference

Novel 15-crown-5 ether or β-diketone incorporated gadolinium complexes for the detection of potassium ions or magnesium and calcium ions

Hifumi, Hiroki; Tanimoto, Akihiro; Citterio, Daniel; Komatsu, Hirokazu; Suzuki, Koji, Analyst (Cambridge, 2007, 132(11), 1153-1160

Production Method 2

87-13-8

109-06-8

88612-71-9

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  -80 °C; -80 °C → -20 °C
1.2 Solvents: o-Xylene ;  reflux

Reference

Quinolizidinone Carboxylic Acids as CNS Penetrant, Selective M1 Allosteric Muscarinic Receptor Modulators

Kuduk, Scott D.; Chang, Ronald K.; Di Marco, Christina N.; Ray, William J.; Ma, Lei; et al, ACS Medicinal Chemistry Letters, 2010, 1(6), 263-267

Production Method 3

87-13-8

109-06-8

88612-71-9

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  30 min, -60 °C
1.2 Solvents: Tetrahydrofuran ;  -60 °C; 2 h, -60 °C → -20 °C

Reference

Discovery of a Selective Allosteric M1 Receptor Modulator with Suitable Development Properties Based on a Quinolizidinone Carboxylic Acid Scaffold

Kuduk, Scott D.; Chang, Ronald K.; Di Marco, Christina N.; Pitts, Daniel R.; Greshock, Thomas J.; et al, Journal of Medicinal Chemistry, 2011, 54(13), 4773-4780

Production Method 4

87-13-8

109-06-8

88612-71-9

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  30 min, rt
1.2 Solvents: Tetrahydrofuran ;  < -60 °C; 2 h, -60 °C → -20 °C

Reference

Programmable late-stage C-H bond functionalization enabled by integration of enzymes with chemocatalysis

Craven, Elliott J.; Latham, Jonathan ; Shepherd, Sarah A. ; Khan, Imtiaz ; Diaz-Rodriguez, Alba; et al, Nature Catalysis, 2021, 4(5), 385-394

Production Method 5

105-53-3

1945-84-2

88612-71-9

Reaction Conditions

1.1 Solvents: Ethanol

Reference

Heterocyclic compounds with bridgehead nitrogen atoms. I. Synthesis of 2-ethynylpyridine and some derived quinolizinones

Leaver, D.; Gibson, W. K.; Vass, J. D. R., Journal of the Chemical Society, 1963, 6053, 6053-6

Production Method 6

101192-15-8

88612-71-9

Reaction Conditions

1.1 Solvents: Xylene ;  48 h, reflux

Reference

A fluorescent activatable probe for imaging intracellular Mg2+

Treadwell, Ryan; de Moliner, Fabio; Subiros-Funosas, Ramon; Hurd, Toby; Knox, Kirsten; et al, Organic & Biomolecular Chemistry, 2018, 16(2), 239-244

Production Method 7

87-13-8

109-06-8

88612-71-9

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  -80 °C → -20 °C
1.2 Solvents: o-Xylene ;  reflux

Reference

Quinolizidinone carboxylic acid selective M1 allosteric modulators: SAR in the piperidine series

Kuduk, Scott D.; Chang, Ronald K.; Di Marco, Christina N.; Ray, William J.; Ma, Lei; et al, Bioorganic & Medicinal Chemistry Letters, 2011, 21(6), 1710-1715

Production Method 8

101192-15-8

88612-71-9

Reaction Conditions

1.1 Solvents: Xylene ;  reflux

Reference

Design, synthesis and anti-HIV integrase evaluation of 4-Oxo-4H-quinolizine-3-carboxylic acid derivatives

Xu, Yi-Sheng; Zeng, Cheng-Chu; Jiao, Zi-Guo; Hu, Li-Ming; Zhong, Ru-gang, Molecules, 2009, 14(2), 868-883

ethyl 4-oxoquinolizine-3-carboxylate Raw materials

• 1,3-diethyl 2-(ethoxymethylidene)propanedioate
• ethyl 3-ethoxy-2-ethoxycarbonyl-4-(pyridin-2-yl)butyrate
• 1,3-diethyl propanedioate
• 2-Ethynylpyridine
• 2-Methylpyridine

ethyl 4-oxoquinolizine-3-carboxylate Preparation Products

• ethyl 4-oxoquinolizine-3-carboxylate (88612-71-9)

• 1. An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction?
  Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui Song Nanoscale, 2020,12, 7024-7034
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  Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu Zhang Anal. Methods, 2020,12, 3376-3381
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolizines Quinolizines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolizines

• 70254-56-7(3-Pyridinecarboxylic acid, 1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxo-,ethyl ester)
• 384831-60-1(Methyl 1,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate)
• 81450-67-1(3-Pyridinecarboxylic acid, 1,2-dihydro-6-methyl-2-oxo-, 1,1-dimethylethyl ester)
• 16108-48-8(Ethyl 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate)
• 54401-76-2(&nbsp;)
• 337909-31-6(4H-Quinolizine-3-carboxylicacid, 8-amino-4-oxo-)
• 51146-04-4(Ethyl 6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate)
• 87762-38-7(3-Pyridinecarboxylic acid, 6-[(diethylamino)carbonyl]-1,2-dihydro-2-oxo-, ethyl ester)
• 337909-10-1(Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate)
• 51146-06-6(methyl 2-hydroxy-6-methylpyridine-3-carboxylate)