Isoquinoline-based amino acid derivatives

Heterocyclic Communications

Volumn 6, Issue 1, 2000, Pages 13-20

  Coppola, Gary M ^a   Zhang, Y Larry ^a   Schuster, Herbert F ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034396815     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2000.6.1.13     Document Type: Article

References (12)

1. M. Shamma, The Isoquinoline Alkaloids, Chemistry and Pharmacology, Academic Press, New York, 1972.
2. F. G. Kathawala, G. M. Coppola and H. F. Schuster (Eds.), Heterocyclic Compounds, Isoquinolines, Part 2, John Wiley, New York, 1990.
3. W. Bartmann, E. Konz and W. Ruger, Heterocycles 29, 707 (1989).
4. H. Suzuki and H. Abe, Synthesis 763 (1995).
5. L. Wessjohann, L. Skattebol and A. de Meijere, J. Chem. Soc., Chem. Commun., 574 (1990).
6. A. Kubo, Y. Kitahara, S. Nakahara, R. Iwata and R. Numata, Chem. Pharm. Bull. 36, 4355 (1988).
7. K. Matsuo, M. Okumura and K. Tanaka, Chem. Pharm. Bull. 30, 4170 (1982).
8. M. Croisy-Delcey, C. Huel and E. Bisagni, J. Heterocyclic Chem. 25, 655 (1988).
9. W. M. Whaley and T. R. Govindachari, Organic Reactions, Vol. 6, John Wiley, New York, 1951.
10. Melting points of crystalline products: 3e, 59-61 °; 4b, 171-174 °;4d, 119-122 °; 4e, 134-135 °; 4f, 102-105 °; 4g, 159-162 °; 4i, 165-167 °; 41, 135-135 °; 6b, 151-153 °; 6c, 140-143 °; 6d, 145-148 °; 6e, 149-151 °; 6f, 132-135 °; 6i, 151-153 °; 6j, 111-115 °; 6k, 45-47 °; 61, 182-184 °; 7b, 178-181 °; 7d, 155-158 °; 7j, 202-204 °; 8b, 230-232 °; 8c, 195-198 °; 8d, 193-196 °; 8e, 251-252 °; 8f, 190-191 °; 8h, 154-156 °; 8i, 201-203 °; 8j; 200-203 °; 8k, 66-67 °; 81, 163-164 °; 10a, 110-113 °; 10b, 169-171 °; 10c, 187-192 °; 10d, 149-152 °; 10e, 147-149 °, 10f, 130-131 °; 10h, 130-131 °; 10i, 163-164 °; 10j, 141-144 °; 10k, 154-155 °; 101, 118-120 °; 17a, 98-100 °; 17c, 110-112 °; The following are di-HCl salts: 9a, 177-179 ° [dec]; 9b, 225-228 ° [dec]; 9d, 260-262 °; 9e, 242-243 °; 9f, 206-208 °; 9g, 193 ° [dec]; 9i, 147-149 °; 9j, 156-159 °; 9k, 151-153 °, 91, 187-188 °; 16a, 220-222 °; 16b, 209-211 °; 16c, 95 ° [dec].
11. In the case of 16c, 5 ml of n-propylamine was used and the reaction stirred at room temperature 21 hr.
12. 3): δ 9.02 (s, 1H), 8.50 (s, 1H), 7.37 (s, 1H), 6.25 (s, broad, 1H), 4.93 (d, 2H), 4.46 (q, 2H), 4.08 (s, 3H), 4.02 (s, 3H), 1.59-1.45 (m, 12H).