The 't-amino effect' of ortho-nitroso amines. Synthesis of 2,6-diaminoadenine derivatives from 6-(Dialkylamino)-5-nitrosopyrimidines

Helvetica Chimica Acta

Volumn 94, Issue 5, 2011, Pages 785-800

  Del Carmen Ruiz, Maria ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

't Amino effect'; Adenine, 2,6 diamino ; Nitroso amines; Purines, 2,6 diamino , tricyclic; Pyrimidines, 6 (dialkylamino) 5 nitroso

Indexed keywords

'T-AMINO EFFECT'; ADENINE, 2,6-DIAMINO-; NITROSO AMINES; PURINES, 2,6-DIAMINO-, TRICYCLIC; PYRIMIDINES, 6-(DIALKYLAMINO)-5-NITROSO-;

AMINES; AROMATIC COMPOUNDS;

AMINATION;

1 PHENYLIMIDAZOLIDINE; 2,6 DIAMINOADENINE DERIVATIVE; 5 NITROSO 6 (3 PHENYLIMIDAZOLIDIN 1 YL)PYRIMIDINE 2,4 DIAMINE; 5 NITROSO 6 (PHENYLSULFANYL)PYRIMIDINE 2,4 DIAMINE; 5 NITROSO 6 (PYRROLIDIN 1 YL)PYRIMIDINE 2,4 DIAMINE; 5,6 DIHYDROPURINO[8,9 A]ISOQUINOLINE 9,11 DIAMINE; 6 (1,4' BIPIPERIDIN 1' YL) 5 NITROSOPYRIMIDINE 2,4 DIAMINE; 6 (3,4 DIHYDROISOQUINOLIN 2(1H) YL) 5 NITROSOPYRIMIDINE 2,4 DIAMINE; 6 (AZEPAN 1 YL) 5 NITROSOPYRIMIDINE 2,4 DIAMINE; 6 (DIALKYLAMINO) 5 NITROSOPYRIMIDINE DERIVATIVE; 6 (MORPHOLIN 4 YL) 5 NITROSOPYRIMIDINE 2,4 DIAMINE; 6 (PHENYLSULFANYL)PYRIMIDINE 2,4 DIAMINE; 6,7,8,9 TETRAHYDROPYRIDO[1,2 E]PURINE 2,4 DIAMINE; 7,8 DIHYDRO 6H PYRROLO[1,2 E]PURINE 2,4 DIAMINE; 7,8,9,10 TETRAHYDRO 6H AZEPINO[1,2 E]PURINE 2,4 DIAMINE; 8,9 DIMETHYL 9H PURINE 2,6 DIAMINE; 9 ETHYL 8 METHYL 9H PURINE 2,6 DIAMINE; 9 METHYL 8 PHENYL 9H PURINE 2,6 DIAMINE; 9 METHYL 8 PROPYL 9H PURINE 2,6 DIAMINE; 9 METHYL 9H PURINE 2,6 DIAMINE; DIAMINE DERIVATIVE; DIETHYL 2,2 [(2,6 DIAMINO 5 NITROSOPYRIMIDIN 4 YL)IMINO]DIACETATE; ETHYL 1 (2,6 DIAMINO 5 NITROSOPYRIMIDIN 4 YL)PIPERIDINE 4 CARBOXYLATE; N 4 BENZYL N 4 METHYL 5 NITROSOPYRIMIDINE 2,4,6 TRIAMINE; N 4 BUTYL N 4 METHYL 5 NITROSOPYRIMIDINE 2,4,6 TRIAMINE; N 4 ETHYL N 4 (1 METHYLETHYL) 5 NITROSOPYRIMIDINE 2,4,6 TRIAMINE; N 4 ETHYL N 4 METHYL 5 NITROSOPYRIMIDINE 2,4,6 TRIAMINE; N 4,N 4 DIETHYL 5 NITROSOPYRIMIDINE 2,4,6 TRIAMINE; N 4,N 4 DIMETHYL 5 NITROSOPYRIMIDINE 2,4,6 TRIAMINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 79955926712     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201100098     Document Type: Article

References (44)

1. N. S. Zefirov, Tetrahedron 1977, 33, 3193.
2. S. Jiang, Z. Janousek, H. G. Viehe, Bull. Soc. Chim. Belg. 1993, 102, 663.
3. B. De Boeck, S. Jiang, Z. Zdenek, H. G. Viehe, Tetrahedron 1994, 50, 7075.
4. K. A. Krasnov, V. G. Kartsev, Russ. J. Org. Chem. 2005, 41, 901.
5. J. Pinnow, Ber. Dtsch. Chem. Ges. 1895, 28, 3039.
6. O. Meth-Cohn, Adv. Heterocycl. Chem. 1996, 65, 1.
7. O. Meth-Cohn, H. Suschitzky, Adv. Heterocycl. Chem. 1972, 14, 211.
8. W. Verboom, D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas 1990, 109, 311.
9. P. Mátyus, P. Éliás, Á. Polonka- Bálint, B. Halász-Dajka, Synthesis 2006, 2625.
10. E. C. Taylor, G. P. Beardsley, Y. Maki, J. Org. Chem. 1971, 36, 3211.
11. E. C. Taylor, Y. Maki, A. McKillop, J. Org. Chem. 1972, 37, 1601
12. R. K. Robins, 'Heterocyclic Compounds', Wiley, New York, 1967, p. 142-144.
13. M. Xu, A. Vasella, Helv. Chim. Acta 2006, 89, 1140
14. M. Xu, F. De Giacomo, T. G. George, D. E. Paterson, A. Vasella, Chem. Commun. 2003, 1452.
15. T. Steinlin, A. Vasella, Helv. Chim. Acta 2009, 92, 588
16. T. Steinlin, A. Vasella, Helv. Chim. Acta 2008, 91, 435
17. T. Steinlin, T. Sonati, A. Vasella, Helv. Chim. Acta 2008, 91, 1879
18. F.-L. Zhang, W. B. Schweizer, M. Xu, A. Vasella, Helv. Chim. Acta 2007, 90, 521.
19. F.-L. Zhang, A. Vasella, Helv. Chim. Acta 2007, 90, 2315.
20. V. Ojea, I. Muinelo, J. M. Quintela, Tetrahedron 1998, 54, 927.
21. M. Noguchi, M. Shirai, K. Nakashima, A. Arai, A. Nishida, H. Yamamoto, A. Kakehi, Tetrahedron 2003, 59, 4581.
22. L. D. Patsenker, I. G. Yermolenko, Y. Y. Artyukhova, V. N. Baumer, B. M. Krasovitskii, Tetrahedron 2000, 56, 7319
23. B. De Boeck, H. G. Viehe, Tetrahedron 1998, 54, 513
24. W. H. N. Nijhuis, W. Verboom, A. Abu El-Fadl, G. J. van Hummel, D. N. Reinhoudt, J. Org. Chem. 1989, 54, 209
25. D. N. Reinhoudt, G. W. Visser, W. Verboom, P. H. Benders, M. L. M. Pennings, J. Am. Chem. Soc. 1983, 105, 4775
26. M. Akiba, Y. Kosugi, T. Takada, J. Org. Chem. 1978, 43, 4472
27. H. Suschitzky, M. E. Sutton, Tetrahedron Lett. 1967, 40, 3933.
28. R. Hull, B. J. Lovell, H. T. Openshaw, A. R. Todd, J. Chem. Soc. 1947, 41.
29. W. B. Cowden, N. W. Jacobsen, Aust. J. Chem. 1979, 32, 2049.
30. G. L. Gibson, S. La Rosa, C. J. Suckling, Tetrahedron Lett. 2003, 44, 1267
31. G. L. Gibson, S. La Rosa, C. J. Suckling, Org. Biomol. Chem. 2003, 1, 1909
32. K. R. Guertin, L. Setti, R. Qi, R. M. Dunsdon, B. W. Dymock, P. S. Jones, H. Overton, M. Taylor, G. Williams, J. A. Sergi, K. Wang, Y. Peng, M. Renzetti, R. Boyce, F. Falconi, R. Garippa, A. R. Olivier, Bioorg. Med. Chem. Lett. 2003, 13, 2895
33. M. Israel, H. K. Protopapa, S. Chatterjee, E. J. Modest, J. Pharm. Sci. 1965, 54, 1626.
34. M. G. Tamari, J. Awruch, Tetrahedron 1968, 24, 3981.
35. B. Roth, J. M. Smith, M. E. Hultquist, J. Am. Chem. Soc. 1950, 72, 1914.
36. I. Perillo, E. Repetto, M. C. Caterina, R. Massa, G. Gutkind, A. Salerno, Eur. J. Med. Chem. 2005, 40, 811.
37. A. Marchal, M. Melguizo, M. Nogueras, A. Sánchez, J. N. Low, Synlett 2002, 255.
38. A. Quesada, A. Marchal, M. Melguizo, J. N. Low, C. Glidewell, Acta Crystallogr. B 2004, 60, 76.
39. A. Marchal, M. Nogueras, A. Sánchez, J. N. Low, L. Naesens, E. De Clercq, M. Melguizo, Eur. J. Org. Chem. 2010, 3823.
40. B. C. Barlaam, R. Ducray, J. G. Kettle, to Astrazeneca AB, U.S. Pat. 2009/0023719 A1, 2009.
41. J. Pabba, B. P. Rempel, S. G. Withers, A. Vasella, Helv. Chim. Acta 2006, 89, 635.
42. J. Weinstock, R. Y. Dunoff, B. Sutton, B. Trost, J. Kirkpatrick, F. Farina, A. S. Straub, J. Med. Chem. 1968, 11, 549.
43. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, J. Appl. Crystallogr. 1999, 32, 115.
44. G. M. Sheldrick, SHELXL97, Program for Refinement of Crystal Structures, University of Göttingen, Göttingen, 1997.