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Volumn 11, Issue 8, 2009, Pages 1745-1748

Straightforward and highly efficient catalyst-free one-step synthesis of 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates, and 6-methylpurines through SNAr-based reactions of 6-halopurines with ethyl acetoacetate

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ACETOACETIC ACID ETHYL ESTER; ESTER; HALOGENATED HYDROCARBON; PURINE DERIVATIVE;

EID: 65249184563     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9002256     Document Type: Article
Times cited : (44)

References (61)
  • 5
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    • Bakkestuen, A. K.; Gundersen, L.-L.; Langli. G.; Liu, F.; Nols0e. J. M. J Bioorg. Med. Chem. Lett. 2000, 10, 1207.
    • (a) Bakkestuen, A. K.; Gundersen, L.-L.; Langli. G.; Liu, F.; Nols0e. J. M. J Bioorg. Med. Chem. Lett. 2000, 10, 1207.
  • 9
    • 65249114039 scopus 로고    scopus 로고
    • Hocek. M.; Nauš, P.; Pohl. R.; Votruba, 1.; Furman. P. A.; Tharnish, P. M.; Otto, M. J. J Med. Chem. 2005, 48, 5869.
    • Hocek. M.; Nauš, P.; Pohl. R.; Votruba, 1.; Furman. P. A.; Tharnish, P. M.; Otto, M. J. J Med. Chem. 2005, 48, 5869.
  • 16
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    • Šilhá, P.; Pohl, R.; Votruba, 1.; Hocek, M. Synthesis 2006, 1848.
    • (d) Šilhá, P.; Pohl, R.; Votruba, 1.; Hocek, M. Synthesis 2006, 1848.
  • 39
    • 0028025536 scopus 로고    scopus 로고
    • Gundersen, L.-L.; Bakkestuen, A. K.; Aasen. A. J.; øveras, H.; Rise, F. Tetrahedron 1994, 50, 9743.
    • (a) Gundersen, L.-L.; Bakkestuen, A. K.; Aasen. A. J.; øveras, H.; Rise, F. Tetrahedron 1994, 50, 9743.
  • 61
    • 65249090661 scopus 로고    scopus 로고
    • Typical procedure for the SNAr-based reaction between the 9-Bn- 6-chloropurine (la) and ethyl acetoacetate (2, 9-Bn-6-chloropurine la (0.5 mmol, anhydrous cesium carbonate or anhydrous potassium carbonate (3.75 mmol, and ethyl acetoacetate 2 (2.5 mmol) were sequentially added to 2 mL of DMSO. The mixture was then stirred at the indicated temperature for the indicated time as shown in Tables 2, 3, and 4 (TLC monitoring, After cooling to room temperature, the resulting mixture was mixed with an ample amount of water (ca. 10 mL, The mixture was then extracted with methylene chloride (3 x 10 mL, The collected organic layers were dried with Na2S04 and the solvent was evaporated in vacuo. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate) to give the desired products 3a, 4a, and 5a, respectively
    • 4 and the solvent was evaporated in vacuo. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate) to give the desired products 3a, 4a, and 5a, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.