A novel solid support for derivatization and subsequent N-alkylation of secondary amines: Preparation of N-alkylated 5- and 6-alkoxy-1,2,3,4-tetrahydroisoquinolines via Mitsunobu reaction

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8569-8572

  Heinonen, Petri ^a   Lönnberg, Harri ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROISOQUINOLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DERIVATIZATION; DRUG SYNTHESIS;

EID: 0343307034     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10286-6     Document Type: Article

References (13)

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2. b) DeWitt, S.H.; Czarnik, A.W. Curr. Opin. Biotechnol. 1995, 6, 640.
3. For a review see: Hemkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron 1996, 52, 4527.
4. Morphy, R.J.; Rankovic, Z.; Rees, D.C. Tetrahedron Lett. 1996, 37, 3209.
5. Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Japan 1967, 40, 935.
6. +), 148 (100%), 132 (25%), 120 (43%), 104 (56%), 91 (33%).
7. Durand, S.; Lusinchi, X.; Moreau, R.C. Bull. Soc. Chim. France 1961, 207, 270.
8. +): 191 (83%), 190 (100%), 162 (15%), 160 (16%), 148 (61%), 120 (28%), 104 (48%)
9. 3, 100 MHz): 155.2, 135.9, 129.2, 127.1, 116.8, 114.5, 96.4, 62.0, 47.8, 43.8, 30.4, 29.5, 25.3, 18.8
10. Sall, D.J.; Grunewald, G.L. J. Med. Chem. 1987, 30, 2208.
11. Tsunoda, T.; Yamamia, Y.; Ito, S. Tetrahedron Lett.1993, 34, 1639.
12. 2 and MeOH (3 × 3 mL each), and dried under reduced pressure.
13. 13C NMR spectroscopy and EI mass spectroscopy.