Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (review)

Chemistry of Heterocyclic Compounds

Volumn 45, Issue 2, 2009, Pages 130-150

  Aksenov, A V ^a   Aksenova, I V ^a  

^a NORTH CAUCASUS FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

1,3,5 triazines; Acylation; Amidines; Azapyrenes; Formylation; Heterocyclization; Imidazoles; Oxazoles; Peri annelation; Perimidines; Pyridines; Pyrimidines; Recyclization; Thiazoles

Indexed keywords

EID: 67650693722     PISSN: 00093122     EISSN: 15738353     Source Type: Journal    
DOI: 10.1007/s10593-009-0243-5     Document Type: Article

References (65)

1. C Grundmann A Kreutzberger 1955 J. Am. Chem. Soc. 77 6559
2. C Grundmann 1963 Angew. Chem., Int. Ed. 2 309
3. L. Hinkel, E. E. Ayling, and J. H. Beynon, J. Chem. Soc., 678 (1935).
4. A. Kreutzberger and M. F. G. Stevens, J. Chem. Soc. (C), 1282 (1969).
5. A Kreutzberger MU Uzbek 1972 Angew. Chem., Int. Ed. 11 144
6. A Kreutzberger MU Uzbek 1972 Arch. Pharm. 305 502
7. C Grundmann R Ratz 1956 J. Org. Chem. 21 1037
8. C Grundmann A Kreutzberger 1955 J. Am. Chem. Soc. 77 44
9. H Weiland H Hess 1909 Ber. 42 4175
10. C Grundmann R Ratz 1958 Chem. Ber. 91 1766
11. H Nohira Y Nishikava Y Furuya T Makaiyama 1965 Bull. Chem. Soc. Jpn. 38 897
12. S. P. Gromov, D. V. Yashunskii, R. S. Sagitullin, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., 1243 (1992). [Chem. Heterocycl. Comp., 28, 1054 (1992)].
13. ER Bilbao M Alvarado Ch F Masaguer E Ravina 2002 Tetrahedron Lett. 43 3551
14. A Kreutzberger C Grundmann 1961 J. Org. Chem. 26 1121
15. KR Huffman FC Schaefer GA Peters 1962 J. Org. Chem. 27 551
16. A Kreutzberger E Kreutzberger 1976 Tetrahedron 32 2603
17. A Kreutzberger E Kreutzberger 1975 Tetrahedron 31 93
18. A Kreutzberger 1967 Angew. Chem., Int. Ed. 6 940
19. L. Fieser and M. Fieser, Reagents for Organic Chemistry [Russian translation], Mir, Moscow (1971), Vol. 5, p. 430.
20. A. V. Aksenov, I. V. Aksenova, I. V. Borovlev, and A. A. Zamorkin, Izv. Akad. Nauk. Ser. Khim., 207 (2008).
21. A Kreutzberger 1971 Arch. Pharm. 304 362
22. AV Aksenov IV Borovlev AS Lyakhovnenko IV Aksenova 2007 Zh. Org. Khim. 43 1581
23. A. V. Aksenov, I. V. Borovlev, A. S. Lyakhovnenko, and I. V. Aksenova, Khim. Geterotsikl. Soedin., 629 (2007). [Chem. Heterocycl. Comp., 43, 527 (2007)].
24. A. V. Aksenov, I. V. Aksenova, D. A. Lobach, and S. V. Shcherbakov, Khim. Geterotsikl. Soedin., 1107 (2008). [Chem. Heterocycl. Comp., 44, 893 (2008)].
25. A. V. Aksenov, I. V. Aksenova, A. S. Lyakhovnenko, and N. A. Aksenov, Khim. Geterotsikl. Soedin., 1694 (2008). [Chem. Heterocycl. Comp., 44, 1379 (2008)].
26. HC Jha F Zilliken E Breitmayer 1981 Angew. Chem., Int. Ed. 20 102
27. I. V. Aksenova, A. V. Aksenov, A. A. Zamorkin, and V. I. Goncharov, Khim. Geterotsikl. Soedin., 260 (2008). [Chem. Heterocycl. Comp., 44, 197 (2008)].
28. AV Aksenov AS Lyakhovnenko IV Aksenova ON Nadein 2008 Tetrahedron Lett. 49 1808
29. M Kurayabashi C Grundmann 1978 Bull. Chem. Soc. Jpn. 51 1484
30. M. Balogh, I. Hermecz, G. Naray-Szabo, K. Simon, and Z. Meszaros, J. Chem. Soc., Perkin Trans. 1, 753 (1986).
31. M Balogh I Hermecz K Simon L Pusztay 1989 J. Heterocycl. Chem. 26 1755
32. J. Kleinschroth, K. Mannhardt, J. Hartenstein, and G. Satzinger, Synthesis, 859 (1986).
33. M Balogh I Hermecz Z Mészáros K Simon L Pusztay G Horváth P Dvortsák 1980 J. Heterocycl. Chem. 17 359
34. A. V. Aksenov, I. V. Borovlev, S. V. Pisarenko, and I. V. Aksenova, Khim. Geterotsikl. Soedin., 1080 (2008). [Chem. Heterocycl. Comp., 44, 868 (2008)].
35. I. V. Aksenova, A. V. Aksenov, and A. S. Lyakhovnenko, Khim. Geterotsikl. Soedin., 947 (2008). [Chem. Heterocycl. Comp., 44, 765 (2008)].
36. FC Schaefer GA Peters 1962 J. Org. Chem. 27 3608
37. FC Schaefer GA Peters 1961 J. Org. Chem. 26 2784
38. FC Schaefer GA Peters 1959 J. Am. Chem. Soc. 81 1470
39. HC Van der Plas 1985 Tetrahedron 41 237
40. S. P. Gromov, D. V. Yashunskii, R. S. Sagitullin, and Yu. G. Bundel', Dokl. Akad. Nauk, 364 (1987).
41. S. P. Gromov, D. V. Yashunskii, R. S. Sagitullin, and A. N. Kost, USSR Inventor's Certificate 1049484; Byul. Izobr., No. 39, 72 (1983).
42. X Liang A Lohse M Bols 2000 J. Org. Chem. 65 7432
43. AV Aksenov IV Borovlev IV Aksenova SV Pisarenko DA Kovalev 2008 Tetrahedron Lett. 49 707
44. A. V. Aksenov, I. V. Borovlev, I. V. Aksenova, and D. A. Kovalev, Khim. Geterotsikl. Soedin., 1590 (2007). [Chem. Heterocycl. Comp., 43, 1353 (2007)].
45. I. V. Borovlev, A. V. Aksenov, I. V. Aksenova, and S. V. Pisarenko, Izv. Akad. Nauk, Ser. Khim., 2275 (2007).
46. AV Aksenov IV Aksenova AA Zamorkin IV Borovlev 2008 Zh. Org. Khim. 44 152
47. A. V. Aksenov, I. V. Aksenova, and A. A. Zamorkin, Khim. Geterotsikl. Soedin., 948 (2008). [Chem. Heterocycl. Comp., 44, 767 (2008)].
48. W. Schaper, Synthesis, 861 (1985).
49. FC Schaefer KR Huffman GA Peters 1962 J. Org. Chem. 27 548
50. DL Boger Q Dang 1992 J. Org. Chem. 57 1631
51. Z Yu Q Dang Yu Wu 2005 J. Org. Chem. 70 998
52. Q Dang Ya Liu Z Sun 2001 Tetrahedron Lett. 42 8419
53. Q Dang BS Brown MD Erion 1996 J. Org. Chem. 61 5204
54. Q Dang Ya Liu MD Erion 1999 J. Am. Chem. Soc. 121 5833
55. C Grundmann A Kreutzberger 1957 J. Am. Chem. Soc. 79 2839
56. A. V. Alekseeva and L. N. Yakhontov, Khim. Geterotsikl. Soedin., 700 (1985). [Chem. Heterocycl. Comp., 21, 593 (1985)].
57. R Gambert Ch Kuratli RE Martin 2004 Tetrahedron Lett. 45 2791
58. DL Boger 1983 Tetrahedron 39 2869
59. DL Boger J Schumacher MD Mullican 1982 J. Org. Chem. 47 2673
60. DL Boger Q Dang 1988 Tetrahedron 44 3379
61. H Neunhoeffer M Bachmann 1975 Chem. Ber. 108 3877
62. H Moehrle M Pycior 1994 Arch. Pharm. 327 533
63. DR Osborn R Levine 1963 J. Org. Chem. 28 2933
64. DR Osborn WT Wieder R Levine 1964 J. Heterocycl. Chem. 1 145
65. H.-J. Schulz, J. Liebscher, and G. Maas, Liebigs Ann. Chem., 411 (1992).