88612-71-9 (4-氧代-4H-羟基嗪-3-羧酸乙酯,ethyl 4-oxoquinolizine-3-carboxylate)

_82%

反应条件：

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

参考文献：

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

合成路线：1 步

_81%

反应条件：

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

参考文献：

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

合成路线：1 步

_80%

反应条件：

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

参考文献：

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

合成路线：1 步

1945-84-2

105-53-3

_28%

反应条件：

1.1 Solvents: Ethanol

参考文献：

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

合成路线：1 步

101192-15-8

_25%

反应条件：

1.1 Solvents: Xylene ; 48 h, reflux

参考文献：

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

合成路线：1 步

反应条件：

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

参考文献：

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

合成路线：1 步

反应条件：

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

参考文献：

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

合成路线：1 步

101192-15-8