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Volumn 46, Issue 35, 2005, Pages 5827-5830

Oxazoline as a useful tool in organic synthesis: Preparation of 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid skeleton

Author keywords

1,6 Conjugate addition; 2 Oxazoline; 4 Aryl 1,2,3,4 tetrahydroisoquinoline

Indexed keywords

AMIDE; ISOQUINOLINE ALKALOID; LITHIUM; OXAZOLINE DERIVATIVE;

EID: 23044481443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.139     Document Type: Article
Times cited : (16)

References (48)
  • 35
    • 23044446038 scopus 로고    scopus 로고
    • Synthesis of 2-alkylbenzoic acids: Alkyllithium additions to 2-vinylbenzoic acid
    • Seijas, J. A.; Vázquez-Tato, M. P.; Martínez, M. M. Synthesis of 2-alkylbenzoic acids: alkyllithium additions to 2-vinylbenzoic acid, Proceedings of ECSOC-2; 1998. http://www.mdpi.net/ecsoc/.
    • (1998) Proceedings of ECSOC-2
    • Seijas, J.A.1    Vázquez-Tato, M.P.2    Martínez, M.M.3
  • 39
    • 23044437362 scopus 로고    scopus 로고
    • note
    • 2, AcOEt/hexane, 3:7), giving 5 (4.07 g, 90%) as a pale yellow oil.
  • 40
    • 23044493336 scopus 로고    scopus 로고
    • note
    • 2, AcOEt/hexane, 3:7), giving compound 5 (279 mg, 63%) as a colorless oil.
  • 41
    • 23044456875 scopus 로고    scopus 로고
    • note
    • In fact, the LUMO energy of the compound without phenyl substituent is lower than that of LUMO+1 for compound with the phenyl group. The addition must take place at LUMO+1, in order to have the appropriate orbital coefficients with lobes on the vinyl group. Orbitals were modeled by Fujitsu, CAChe Pro, version 6.1, based on PM3 Hamiltonian.
  • 42
    • 23044475810 scopus 로고    scopus 로고
    • note
    • 2, AcOEt/hexane, 3:7) giving 7 (91 mg, 60%) as a yellow oil.
  • 43
    • 23044516538 scopus 로고    scopus 로고
    • note
    • 2, AcOEt/hexane, 3:7), giving compound 8 (34 mg, 80% yield) as a white solid.
  • 44
    • 23044491294 scopus 로고    scopus 로고
    • note
    • 2, AcOEt/hexane, 4:6), giving 2-methyl-4- phenyltetrahydroisoquinoline (1a ) (57 mg, 92%) as a viscous oil.
  • 45
    • 23044499351 scopus 로고    scopus 로고
    • note
    • 15NO calcd. (%): C, 80.98; H, 6.37; N, 5.90, found C, 80.53; H, 6.60; N: 5.93.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.