Synthesis of the 2H-quinolizin-2-one scaffold via a stepwise acylation-intramolecular annulation strategy

Tetrahedron Letters

Volumn 47, Issue 29, 2006, Pages 5063-5067

  Natarajan, Swaminathan R ^a   Chen, Meng Hsin ^a   Heller, Stephen T ^a   Tynebor, Robert M ^a   Crawford, Ellen M ^a   Minxiang, Cui ^b   Kaizheng, Han ^b   Dong, Jingchao ^b   Hu, Bin ^b   Hao, Wu ^b   Chen, Shu Hui ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b WuXi Pharmatech ^*  (China)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; QUINOLIZINE DERIVATIVE;

ACYLATION; ANNULATION REACTION; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLIZATION; DEPROTECTION REACTION; SYNTHESIS;

EID: 33745114654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.089     Document Type: Article

References (10)

1. For use of benzo-quinolizinones as CFTR channel inhibitors see. Marivingt-Mounir C., Norez C., Derand R., Bulteau-Pignoux L., Nguyen-Huy D., Viossat B., Morgant G., Becq F., Vierfond J.-M., and Mettey Y. J. Med. Chem. 47 (2004) 962 and references therein
2. Calculated values determined using ACD Labs. The calculated Log D values for hydroxy naphthalene, hydroxy quinoline, and pyrimido-pyrimidine templates as indicated in Figure 1 range from 1.5 to 2.5 at pH 7. Experimentally determined Log D values for similar analogs are in agreement.
3. Calculated dipole moments for the 2H-quinolizinone scaffold (1) was 7.5 Debye units compared to hydroxy naphthalene (2), hydroxy quinoline (3), and pyrimido-pyrimidine (4) at 1.7, 6.7, and 4.6 Debye units, respectively.
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10. 3OD): 8.58 (d, J = 9.6 Hz, 1H); 8.20 (m, 1H); 8.01 (m, 1H); 7.71-7.52 (m, 6H); 7.49 (m, 2H).