Unexpected alternative direction of a Biginelli-like multicomponent reaction with 3-amino-1,2,4-triazole as the urea component

Tetrahedron Letters

Volumn 51, Issue 16, 2010, Pages 2095-2098

  Gorobets, Nikolay Yu ^a,b   Sedash, Yuriy V ^a   Ostras, Konstantin S ^a   Zaremba, Oleg V ^c   Shishkina, Svetlana V ^a   Baumer, Vyacheslav N ^a   Shishkin, Oleg V ^a   Kovalenko, Sergiy M ^c   Desenko, Sergey M ^a   Van der Eycken, Erik V ^b  

^a INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c NATIONAL UNIVERSITY OF PHARMACY   (Ukraine)

Author keywords

3 Amino 1,2,4 triazole; Biginelli condensation; Microwave assisted organic synthesis; Multicomponent reaction

Indexed keywords

AMITROLE; UREA;

ARTICLE; BIGINELLI REACTION; CRYSTAL STRUCTURE; MICROWAVE IRRADIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 77949491009     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.045     Document Type: Article

References (24)

1. For a review see:. Kappe C.O. Eur. J. Med. Chem. 35 (2000) 1043-1052
2. For review articles see:. Chebanov V.A., Desenko S.M., and Gurley T.W. Azaheterocycles Based on α,β-Unsaturated Carbonyls (2008), Springer, Berlin, Heiderberg Chapter 3, pp. 61-148
3. Desenko S.M. Chem. Heterocycl. Compd. 31 (1995) 125-136
4. Mourad A.-F.E., Aly A.A., Farag H.H., and Beshr E.A. Beilstein J. Org. Chem. 3 (2007) 1-5
5. Chebanov V.A., Muravyova E.A., Desenko S.M., Musatov V.I., Knyazeva I.V., Shishkina S.V., Shishkin O.V., and Kappe C.O. J. Comb. Chem. 8 (2006) 427-434
6. Lipson V.V., Desenko S.M., Borodina V.V., Shirobokova M.G., and Musatov V.I. Russ. J. Org. Chem. 41 (2005) 114-119
7. Fedorova O.V., Zhidovinova M.S., Rusinov G.L., and Ovchinnikova I.G. Russ. Chem. Bull. Int. Ed. 52 (2003) 1768-1769
8. Zhidovinova M.S., Fedorova O.V., Rusinov G.L., and Ovchinnikova I.G. Mol. Div. 6 (2003) 323-326
9. Gein V.L., Gein L.F., and Tsyplyakova E.P. Chem. Heterocycl. Compd. 39 (2003) 821-822
10. Lipson V.V., Desenko S.M., Shirobokova M.G., and Borodina V.V. Chem. Heterocycl. Compd. 39 (2003) 1213-1217
11. Shaabani A., Farhangi E., and Rahmati A. Comb. Chem. High Throughput Screen. 9 (2006) 771-776
12. For the application of salicylic aldehydes in Biginelli reactions see:. Kumar A., and Maurya R.A. Tetrahedron Lett. 48 (2007) 4569-4571
13. Renwei Z., Xiaoxia W., Hui X., and Jingxing D. Synth. Commun. 36 (2006) 1503-1513
14. Bose D.S., Kumar R.K., and Fatima L. Synlett (2004) 279-282
15. Fu N.-Y., Yuan Y.-F., Pang M.-L., Wang J.-T., and Peppe C. J. Organomet. Chem. 672 (2003) 52-57
16. Fu N.-Y., Yuan Y.-F., Cao Z., Wang S.-W., Wang J.-T., and Peppe C. Tetrahedron 58 (2002) 4801-4807
17. Rehani R., Shah A.C., and Arya V.P. Indian J. Chem. B 33 (1994) 775-778
18. Svetlik J., Hanus V., and Bella J. J. Chem. Res. (S) (1991) 4-5
19. Kleinpeter E., Koch A., Fischer G., and Askolin C.-P. J. Mol. Struct. 435 (1997) 65-76
20. Allen C.F.H., Beilfuss H.R., Burness D.M., Reynolds G.A., Tinker J.F., and VanAllan J.A. J. Org. Chem. 24 (1959) 787-793
21. Cipens G., and Grinsteins V. Zh. Obshch. Khim. 32 (1962) 460-464 Chem. Abstr. 1962, 58, 3276
22. Dallinger D., and Kappe C.O. Nat. Protoc. 2 (2007) 1713-1721
23. Stadler A., and Kappe C.O. J. Comb. Chem. 3 (2001) 624-630
24. For a detailed study of compounds 10a, b, and11 using HSQC, HMBC, COSY, and NOESY experiments see the Supplementary data.