Solid phase synthesis of tetrahydroisoquinolines and tetrahydroimidazopyridines

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4865-4868

  Hutchins, Steven M ^a   Chapman, Kevin T ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HISTAMINE DERIVATIVE; IMIDAZOPYRIDINE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; TYRAMINE;

ARTICLE; CYCLIZATION; DRUG PURITY; DRUG SYNTHESIS;

EID: 0030575349     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00996-3     Document Type: Article

References (11)

1. 1. (a) Kametani, T. and Fukumoto, K. Heterocyles 1975, 3(4), 311-341.
2. (b) Fogelman, F. and Grundy, H. F. Br. J. Pharmac. 1970, 38, 416-432.
3. (c) Winter, C. A. and Lehman, J. T. J. Pharm. Exp. Ther. 1950, 100, 489-501.
4. (d) Hope, E.; Pyman, F. L.; Remfry, F. G. P. and Robinson, R. J. Chem. Soc. 1931, 236-247.
5. 2. Kametani, T.; Koizumi, M.; Okui, K.; Nishii, Y and Ono, M. J. Med. Chem. 1972, 15(2), 203-204
6. 3. Meutermans, W. D. F. and Alewood, P. F. Tetrahedron Lett. 1995, 36(42), 7709-7712.
7. 4. Kametani, T.; Kigasawa, K.; Hiiragi, M. and Ishimaru, H. J. Chem. Soc. (C) 1971, 2632.
8. 5. The resin used was purchased from Rapp Polymere (Polyethyleneglycol spacer on a polystyrene bead (130 micron, 0.23 mmol/g) - TentaGel S RAM Fmoc - cat. # S30023).
9. 6. Zuckermann, R. N.; Kerr, J. M.; Kent, S. B. H. and Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646-10647.
10. 7. HPLC Conditions: 10 - 100% acetonitrile in water + 0.1% trifluoroacetic acid, linear gradient over 10 minutes, flow rate: 1.5 mL/min, Zorbax SB C8 column (4.6 mm x 7.5 cm), 230 nm.
11. 8. All samples were run on a Finnigan MAT TSQ700 using electrospray ionization.