Unusual stabilization of 1,2-diamino derivatives of quincorine and quincoridine by carbon dioxide: Persistent crystalline prim-ammonium-carbamate salts and their reactivity towards isatoic acid anhydride

European Journal of Organic Chemistry

Volumn , Issue 19, 2003, Pages 3784-3790

  Neda, Ion ^a   Kaukorat, Thomas ^a   Fischer, Axel K ^b  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b OTTO VON GUERICKE UNIVERSITY   (Germany)

Author keywords

Amino alcohols; Carboxylation; Nitrogen heterocycles

Indexed keywords

ACID ANHYDRIDE; AMMONIUM CARBAMATE DERIVATIVE; AMMONIUM DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBON DIOXIDE; HETEROCYCLIC COMPOUND; ISATOIC ACID ANHYDRIDE; QUINCORIDINE DERIVATIVE; QUINCORINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; GEOMETRY; HYDROGEN BOND; HYDROPHILICITY; MOLECULAR STABILITY; SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0141960453     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300211     Document Type: Article

References (28)

1. [1a] H. M. R. Hoffmann, O. Schrake, Tetrahedron: Asymmetry 1998, 9, 1051-1057.
2. [1b] O. Schrake, W. M. Braje, R. Wartchow, H. M. R. Hoffmann, Tetrahedron: Asymmetry 1998, 9, 3717-3722.
3. [1c] C. von Riesen, R. Wartchow, H. M. R. Hoffmann, Z. Kristallogr. NCS 1998, 213, 483-484.
4. [1d] R. Wartchow, O. Schrake, W. M. Braje, H. M. R. Hoffmann, Z. Kristallogr NCS 1999, 214, 285-286.
5. [1e] O. Schrake, V. S. Rahn, J. Frackenpohl, W. M. Braje, H. M. R. Hoffmann, Org. Lett. 1999, 1, 1607-1610.
6. [1f] O. Schrake, M. H. Franz, R. Wartchow, H. M. R. Hoffmann, Tetrahedron 2000, 56, 4453-4465.
7. [1g] W. M. Braje, I. Frackenpohl, O. Schrake, R. Wartchow, W. Beil, H. M. R. Hoffmann, Helv. Chim. Acta 2000, 83, 777-792.
8. [1h] J. Frackenpohl, S. Röper, H. M. R. Hoffmann, R. Wartchow, Z. Kristallogr. New Cryst. Struct. 2000, 215, 437-438.
9. [1i] S. Röper, J. Frackenpohl, O. Schrake, R. Wartchow, H. M. R. Hoffmann, Org. Lett. 2000, 2, 1661-1664.
10. H. M. R. Hoffmann, T. Plessner, C. von Riesen, Synlett 1996, 690-692.
11. I. Neda, T. Kaukorat, C. Hrib, Tetrahedron: Asymmetry 2002, 13, 1327-1330.
12. M. Manhas, S. Amin, J. Heterocycl. Chem. 1977, 14, 161-164.
13. S. Hayao, H. Harere, W. Strycker, T. Leipzig, R. Kulp, H. Hartzler, J. Med. Chem. 1965, 8, 807-812.
14. A. Santilli, J. Osdene, J. Org. Chem. 1964, 29, 2717-2720.
15. M. Gibson, M. Green, Tetrahedron 1965, 21, 2191-2195.
16. N. Heindel, T. Lemke, J. Heterocycl. Chem. 1966, 3, 389-402.
17. I. Neda, T. Kaukorat, R. Schmutzler, U. Niemeyer, B. Kutscher, J. Pohl, J. Engel, Phosphorus, Sulfur and Silicon 2000, 162, 81-218.
18. N. Brock, Cancer Res. 1989, 49, 1-28.
19. G. Hardtmann, G. Koletar, O. Pfister, J. Heterocycl. Chem. 1975, 12, 565-576 and references cited therein.
20. P. Rademacher, K. Kowski, H. M. R. Hoffmann, L. O. Haustedt, J. Holzgrefe, ChemPhysChem 2002, 3, 957-962.
21. L. Knorr, Ann. Chem. 1898, 301, 1-18.
22. C. J. Brown, L. R. Gray, Acta Crystallogr, Sect. B 1982, 38, 2307-2308.
23. M. Czugler, P. Bombicz, I. Csoregh, O. Gallardo, Z. Kristallogr 1995, 210, 368-369.
24. R. B. von Dreele, R. L. Bradshaw, W. J. Burke, Acta Crystallogr., Sect. C 1983, 39, 253-255.
25. M. Freytag, P. G. Jones, Acta Crystallogr., Sect. C 1999, 55, 1874-1877.
26. W. Schroth, H.-D. Schädler, J. Andersch, Z. Chem. 1989, 29, 129-135.
27. G. M. Sheldrick, SHELXTL, Structure Determination Software Programs, Version 5.03 (PC), Siemens Analytical X-Ray Instruments, Madison, WI, USA, 1995.
28. G. M. Sheldrick, SHELXL-97. A program for crystal structure refinement, Universität Göttingen, 1997.