The synthesis of N-(pyridylamino)tetrahydroisoquinolines and benzazepines via the Pictet-Spengler cyclization

Synlett

Volumn , Issue 1, 2000, Pages 137-139

  Merriman, Gregory H ^a   Fink, David M ^a   Freed, Brian S ^a   Kurys, Barbara E ^a   Pavlek, Shelly ^a   Varriano, Jennifer ^a   Paulus, Erich F ^b  

^a Medicinal Chemistry   (United States)

^b Hoechst Marion Roussel D ^*  (Germany)

Author keywords

Benzazepines; Chloromethyl methyl ether; Pictet Spengler; Tetrahydroisoquinolines; Tetrazines

Indexed keywords

ALPHA 2 ADRENERGIC RECEPTOR BLOCKING AGENT; BENZAZEPINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; N (PYRIDYLAMINO)TETRAHYDRISOQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033966805     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (12)

1. For the synthesis of homophthalic anhydrides see: a) Inamadar, S. P.; Usagaonkar, R. N., J. Indian Chem. Soc. 1963, 40, 239,
2. b) Inamadar, S. P.; Usagaonkar, R. N., J. Indian Chem. Soc. 1966, 43, 615.
3. Pictet, A.; Spengler, T. Ber. 1911, 44, 2030.
4. 1,2,3,4-Tetrahydophthalazines have been prepared via hydrazine and hydrazide cyclization: Kametani, T.; Kigasawa, K.; Hiiragi, M.; Ishimaru, H.; Uryu, T.; Haga, S. J. Chem. Soc., Perkin Trans' 1973, 471.
5. Wunsch, B.; Nerdinger, S. Arch. Pharm. 1995, 328, 301.
6. For the preparation of 4-hydrazinopyridines see: Koenigs, E.; Wiess, W.; Zscharn, A., Chem. Ber. 1926, 316.
7. For the use of MOMCl in the P-S reaction see: Jaques, B.; Deeks, R. H.; Shah, P. K. J. J. Chem. Soc., Chem. Commun. 1969, 1283.
8. 3O: C, 76.11; H, 6.39; N, 12.68; found: C, 75.45; H, 6.45; N, 12.64.
9. Semmelhack, M. F.; Helquist, P.; Jones, L. D.; Keller, L.; Mendelson, L. J. Am Chem. Soc. 1981, 6460.
10. 2: C, 71.35; H, 7.11; N, 15.60; found: C, 70.85; H, 6.90; N, 15.47.
11. The formation of tetrazines via dimerization of hydrazines using formaldehyde is well precedented: Knorr, L.; Weidel, A. Chem. Ber. 1909, 42, 3525.
12. For a discussion of the conformations of hexahydro-1,2,4,5-tetrazines see: Riddel, F. G. The Conformational Analysis of Heterocyclic Compounds; Academic: London, 1980; p 92 and references cited therein.