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Volumn 23, Issue 16, 2012, Pages 2408-2412

Ring Opening of Cyclic Sulfamidates with Magnesiated Heterocycles: Expedient Synthesis of Highly Functionalised Azaindolines and Azatetrahydroquinolines

Author keywords

azaindoline; cyclic sulfamidate; metalation; pyrimidine; ring opening

Indexed keywords

AZAINDOLINE DERIVATIVE; AZATETRAHYDROQUINOLINE DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; MAGNESIATED CHLOROPYRIDINE DERIVATIVE; MAGNESIATED CHLOROPYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SULFAMIDE DERIVATIVE; UNCLASSIFIED DRUG; AMIDE; SULFAMIDATE DERIVATIVE;

EID: 84865811345     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317170     Document Type: Article
Times cited : (16)

References (32)
  • 1
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    • 3 saturation and the probability of clinical success, see: Lovering F., Bikker J., Humblet C. J. Med. Chem.: 2009; 52 6752
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    • Lovering, F.1    Bikker, J.2    Humblet, C.3
  • 20
    • 80052577435 scopus 로고    scopus 로고
    • For a recent application, including a comparison with N-protected aziridines, see
    • For a recent application, including a comparison with N-protected aziridines, see: Hebeisen P., Weiss U., Alker A., Staempfli A. Tetrahedron Lett.: 2011; 52 5229
    • (2011) Tetrahedron Lett. , vol.52 , pp. 5229
    • Hebeisen, P.1    Weiss, U.2    Alker, A.3    Staempfli, A.4
  • 31
    • 72049122384 scopus 로고    scopus 로고
    • Generally, activation by strong Lewis acids or formation of the azetidinium ion is necessary
    • Generally, activation by strong Lewis acids or formation of the azetidinium ion is necessary: Couty F., Evano G. Synlett: 2009; 3053
    • (2009) Synlett , pp. 3053
    • Couty, F.1    Evano, G.2
  • 32
    • 85041493379 scopus 로고    scopus 로고
    • Representative Procedure for the Synthesis of Azaindoline 12: To an oven-dried three-necked flask containing 4,6-dichloro-2-(thiomethyl)pyrimidine (1; 390 mg, 2.0 mmol) in anhyd THF (7.5 mL) was added TMPMgClLiCl (1 M in THF, 2.4 mL, 2.4 mmol) at r.t. After stirring for 30 min, tert-butyl (4 S)-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (5; 498 mg, 2.10 mmol) was added and the reaction was stirred for a further 1 h at r.t. 1 N Citric acid (7.5 mL) and EtOAc (7.5 mL) were added, and the reaction was stirred vigorously for 5 min before separation of the layers. The organic layer was concentrated, then the residue was stirred in TFA (5 mL) for 15 min before again being concentrated
    • 3ClS: 216.03567; found: 216.03557


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.