Reaction of 1-substituted 3,5-diamino-1,2,4-triazoles with β-keto esters: synthesis and new rearrangement of mesoionic 3-amino-2H-[1,2,4]triazolo-[4,3-a]pyrimidin-5-ones

Tetrahedron

Volumn 66, Issue 18, 2010, Pages 3301-3313

  Chernyshev, Victor M ^a   Astakhov, Alexander V ^a   Starikova, Zoya A ^b  

^a PLATOV SOUTH RUSSIAN STATE POLYTECHNIC UNIVERSITY NPI   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Keto esters; 1 Substituted 1H 1,2,4 triazole 3,5 diamines; 1,2,4 Triazolo 4,3 a pyrimidin 5 ones; Condensation; Mesoionic; Rearrangement

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL;

EID: 77950457603     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.009     Document Type: Article

References (80)

1. Yamashkin S.A., Kucherenko N.Y., and Yurovskaya M.A. Chem. Heterocycl. Compd. (Engl. Transl.) 33 (1997) 499-514
2. Hajós G., and Riedl Z. In: Katritzky A.R., Ramsden C.A., Scriven E.F.V., and Taylor R.J.K. (Eds). Comprehensive Heterocyclic Chemistry III Vol. 11 (2008), Elsevier, Oxford 671-763
3. Riggs R.L., and Smith D.M. In: Katritzky A.R., Ramsden C.A., Scriven E.F.V., and Taylor R.J.K. (Eds). Comprehensive Heterocyclic Chemistry III Vol. 12 (2008), Elsevier, Oxford 857-973
4. Metwally M.A., Abdel-Latif E., Amer F.A., and Kaupp G. J. Sulfur Chem. 25 (2004) 63-85
5. Awadallah F.M. Sci. Pharm. 76 (2008) 415-438
6. Nam N.L., Grandberg I.I., and Sorokin V.I. Chem. Heterocycl. Compd. (Engl. Transl.) 39 (2003) 1210-1212
7. Shiota T., Yamamori T., Sakai K., Kiyokawa M., Honma T., Ogawa M., Hayashi K., Ishizuka N., Matsumura K., Hara M., Fujimoto M., Kawabata T., and Nakajima S. Chem. Pharm. Bull. 47 (1999) 928-938
8. Mukaiyama H., Nishimura T., Shiohara H., Kobayashi S., Komatsu Y., Kikuchi S., Tsuji E., Kamada N., Ohnota H., and Kusama H. Chem. Pharm. Bull. 55 (2007) 881-889
9. Fischer G. Adv. Heterocycl. Chem. 95 (2007) 143-219
10. Reiter J., Pongó L., and Dvortsák P. Tetrahedron 43 (1987) 2497-2504
11. Esses-Reiter K., and Reiter J. J. Heterocycl. Chem. 24 (1987) 1503-1508
12. Reiter J., and Rivó E. J. Heterocycl. Chem. 25 (1988) 1497-1502
13. Reiter J., Pongó L., Somorai T., and Pallagi I. Monatsh. Chem. 121 (1990) 173-187
14. Fischer G. Adv. Heterocycl. Chem. 57 (1993) 81-138
15. Revankar G.R., and Robins R.K. In: Townsend L.B. (Ed). Chemistry of Nucleosides and Nucleotides Vol. 2 (1988), Plenum, New York, NY 161-398
16. Shaban M.A.E. Adv. Heterocycl. Chem. 70 (1997) 163-337
17. Revankar G.R., Robins R.K., and Tolman R.L. J. Org. Chem. 39 (1974) 1256-1262
18. Akhondzadeh S., Malek-Hosseini M., Ghoreishi A., Raznahan M., and Rezazadeh S.-A. Prog. Neuropsychopharmacol. Biol. Psychiatry 32 (2008) 1879-1883
19. Hafez H.N., Abbas H.-A.S., and El-Gazzar A.-R.B.A. Acta Pharm. 58 (2008) 359-378
20. El-Gazzar A.-R.B.A., Hussein H.A.R., and Hafez H.N. Acta Pharm. 57 (2007) 395-411
21. El-Gazzar A.-R.B.A., and Hafez H.N. Acta Chim. Slov. 55 (2008) 359-371
22. Soliman F.S.G., Shafik R.M., and Darwish M. J. Pharm. Sci. 71 (1982) 178-182
23. Ravindra K.C., Vagdevi H.M., and Vaidya V.P. ARKIVOC xi (2008) 1-10
24. Suiko M., Hayashida S., and Nakatsu S. Agric. Biol. Chem. 46 (1982) 2691-2695
25. Magán R., Marin C., Salas J.M., Barrera-Pérez M., Rosales M.J., and Sánchez-Moreno M. Mem. Inst. Oswaldo Cruz 99 (2004) 651-656
26. Łakomska I. Inorg. Chim. Acta 362 (2009) 669-681
27. Zhai X., Zhao Y.-F., Liu Y.-J., Zhang Y., Hun F.-Q., Liu J., and Gong P. Chem. Pharm. Bull. 56 (2008) 941-945
28. Phillips M.A., Gujjar R., Malmquist N.A., White J., El Mazouni F., Baldwin J., and Rathod P.K. J. Med. Chem. 51 (2008) 3649-3653
29. Cavallaro C.L., Harikrishnan L.S., Chi F., Dodd D., and Purandare A. J. Comb. Chem. 10 (2008) 28-30
30. Papini P. Gazz. Chim. Ital. 80 (1950) 100-106
31. Papini P., and Checchi S. Gazz. Chim. Ital. 80 (1950) 850-854
32. Papini P. Gazz. Chim. Ital. 82 (1952) 735-745
33. Bavley, A. U.S. Patent 2,406,654, 1946; Chem. Abstr. 1947, 41, 42h.
34. Shaban M.A.E., and Morgaan A.E.A. Adv. Heterocycl. Chem. 73 (1999) 131-176
35. Golubushina G.M., Poshtaruk G.N., and Chuiguk V.A. Chem. Heterocycl. Compd. (Engl. Transl.) 10 (1974) 491-494
36. Bratulescu G. Synthesis (2005) 2833-2834
37. Chernyshev V.M., Rakitov V.A., Taranushich V.A., and Blinov V.V. Chem. Heterocycl. Compd. (Engl. Transl.) 41 (2005) 1139-1146
38. Chernyshev V.M., Kosov A.E., Gladkov E.S., Shishkina S.V., Taranushich V.A., Desenko S.M., and Shishkin O.V. Russ. Chem. Bull. (Engl. Transl.) 55 (2006) 338-344
39. Chernyshev V.M., Rakitov V.A., Astakhov A.V., Sokolov A.N., Zemlyakov N.D., and Taranushich V.A. Russ. J. Appl. Chem. (Engl. Transl.) 79 (2006) 624-630
40. Chernyshev V.M., Rakitov V.A., Taranushich V.A., and Starikova Z.A. Chem. Heterocycl. Compd. (Engl. Transl.) 43 (2007) 776-780
41. Minkin V.I., Garnovskii A.D., Elguero J., Katritzky A.R., and Denisko O.V. Adv. heterocycl. Chem. 76 (2000) 157-323
42. Reiter J., Pongó L., and Lukovits I. Monatsh. Chem. 119 (1988) 341-348
43. Reiter J., Pongó L., and Dvortsák P. J. Heterocycl. Chem. 24 (1987) 1149-1154
44. Reiter J., Somorai T., Jerkovich G., and Dvortsák P. J. Heterocycl. Chem. 19 (1982) 1157-1164
45. Reiter J., Somorai T., Dvortsák P., and Bujtás G. J. Heterocycl. Chem. 22 (1985) 385-394
46. Reiter J., Pongó L., Somorai T., and Dvortsák P. J. Heterocycl. Chem. 23 (1986) 401-408
47. Chiara J.L., and Gómez-Sánchez A. In: Rappoport Z. (Ed). The Chemistry of Enamines (1994), Wiley, Chichester 279-404
48. Vainiotalo P., Savolainen P.-L., Ahlgrén M., Mälkönen P.J., and Vepsäläinen J. J. Chem. Soc., Perkin Trans. 2 (1991) 735-741
49. Bartoli G., Cimarelli C., Dalpozzo R., and Palmieri G. Tetrahedron 51 (1995) 8613-8622
50. Kumar R., Maulik P.R., and Misra A.K. J. Carbohydr. Chem. 26 (2007) 83-90
51. Kascheres C.M. J. Braz. Chem. Soc. 14 (2003) 945-969
52. El Ashry E.S.H., El Kilany Y., Rashed N., and Assafir H. Adv. Heterocycl. Chem. 75 (1999) 79-165
53. El Ashry E.S.H., and Rashed N. Adv. Heterocycl. Chem. 72 (1998) 127-224
54. Gizatullina E.M., and Kartsev V.G. Chem. Heterocycl. Compd. (Engl. Transl.) 29 (1993) 1369-1392
55. Danagulyan G.G. Chem. Heterocycl. Compd. (Engl. Transl.) 41 (2005) 1205-1236
56. Van der Plas H.C. Acc. Chem. Res. 11 (1978) 462-468
57. Van der Plas H.C. Adv. Heterocycl. Chem. 74 (1999) 1-253
58. Van der Plas H.C. J. Heterocycl. Chem. 37 (2000) 427-438
59. Maiboroda D.A., and Babaev E.V. Chem. Heterocycl. Compd. (Engl. Transl.) 31 (1995) 1251-1279
60. Babaev E.V., and Zefirov N.S. Chem. Heterocycl. Compd. (Engl. Transl.) 28 (1992) 671-689
61. Babaev E.V., and Zefirov N.S. J. Math. Chem. 11 (1992) 65-78
62. Babaev E.V., Lushnikov D.E., and Zefirov N.S. J. Am. Chem. Soc. 115 (1993) 2416-2427
63. Iyer R.N., and Venkataraman K. Proc. Indian. Acad. Sci. 37 (1953) 629-642
64. Butler R.N. Can. J. Chem. 51 (1973) 2315-2322
65. Berecz G., and Reiter J. J. Heterocycl. Chem. 38 (2001) 237-252
66. Berecz G., Reiter J., Argay G., and Kálmán A. J. Heterocycl. Chem. 39 (2002) 319-325
67. Vas'kevich R.I., Savitskii P.V., Zborovskii Y.L., Staninets V.I., Rusanov E.B., and Chernega A.N. Russ. J. Org. Chem. 42 (2006) 1403-1408
68. Hassaneen H.M., Abdelhadi H.A., and Abdallah T.A. Tetrahedron 57 (2001) 10133-10138
69. Elwan N.M., Awad E.M., Hassaneen H.M., Linden A., and Heimgartner H. Helv. Chim. Acta 86 (2003) 739-749
70. Oganisyan A.S., Noravyan A.S., Karapetyan A.A., Aleksanyan M.S., and Struchkov Y.T. Chem. Heterocycl. Compd. (Engl. Transl.) 40 (2004) 79-83
71. Markosyan A.I., Kuroyan R.A., Dilanyan S.V., Aleksanyan M.S., Karapetyan A.A., and StruchkovYu T. Chem. Heterocycl. Compd. (Engl. Transl.) 36 (2000) 574-578
72. Shawali A.S., Ali N.A.H., Ali A.S., and Osman D.A. J. Chem. Res. (2006) 327-332
73. Burke-Laing M., and Laing M. Acta Crystallogr., Sect. B 32 (1976) 3216-3224
74. Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., and Taylor R. J. Chem. Soc., Perkin Trans. 2 (1987) S1-S19
75. Dunstan A.R., Weber H.-P., Rihs G., Widmer H., and Dziadulewicz E.K. Tetrahedron Lett. 39 (1998) 7983-7986
76. Chernyshev V.M., Rakitov V.A., Blinov V.V., Taranushich V.A., and Starikova Z.A. Chem. Heterocycl. Compd. (Engl. Transl.) 45 (2009) 436-444
77. Sato Y., Shimoji Y., Fujita H., Nishino H., Mizuno H., Kobayashi S., and Kumakura S. J. Med. Chem. 23 (1980) 927-937
78. Steck E.A., Brundage R.P., and Fletcher L.T. J. Am. Chem. Soc. 80 (1958) 3929-3931
79. Fuentes J.J., and Lenoir J.A. Can. J. Chem. 54 (1976) 3620-3625
80. Güzel O., Innocenti A., Scozzafava A., Salman A., Parkkila S., Hilvo M., and Supuran C.T. Bioorg. Med. Chem. 16 (2008) 9113-9120