New syntheses of 4(5)-aryl-5(4)-(2-chromonyl)-1,2,3-triazoles from 2- styrylchromones and sodium azide

Heterocycles

Volumn 51, Issue 3, 1999, Pages 481-487

  Silva, Artur M S ^a   Vieira, Judite S ^a   Cavaleiro, José A S ^a   Patonay, Tamás ^b   Lévai, Albert ^b   Elguero, José ^c  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF DEBRECEN   (Hungary)

^c INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

TRIAZOLE DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR RECOGNITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033102398     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-8423     Document Type: Article

References (16)

1. H. Wamhoff, "Comprehensive Heterocyclic Chemistry", ed. by A. R. Katritzky and C. W. Rees, Vol. 4, ed. by K. V. Potts, Pergamon Press, Oxford, 1984, pp. 669-732.
2. T. L. Gilchrist and G. E. Gymer "Advances in Heterocyclic Chemistry", ed. by A. R. Katritzky and A. J. Boulton, Vol. 16, Academic Press, New York, 1974, pp. 33-88.
3. L. Birkofer and A. Ritter, Angew. Chem., 1965, 77, 414.
4. P. K. Kadaba, Synthesis, 1973, 71.
5. a) J. S. Meck and J. S. Fowler, J. Amer. Chem. Soc., 1967, 89, 1967.
6. b) V. G. L'Abbé and A. Hassner, Angew. Chem., 1971, 83, 103.
7. c) A. Hassner, "Azides and Nitrenes - Reactivity and Utility", ed. by E. F. V. Scriven, Academic Press, Florida, 1984, pp. 35-94.
8. L. A. Badovskaya, G. D. Krapivin, T. Y. Kaklugina, V. G. Kulnevitch and G. F. Muzychenko, Zhur. Org. Khim., 1975, 11, 2445.
9. a) D. C. G. A. Pinto, A. M. S. Silva and J. A. S. Cavaleiro, J. Heterocycl. Chem., 1996, 33, 1887.
10. b) D. C. G. A. Pinto, A. M. S. Silva, L. M. P. M. Almeida, J. A. S. Cavaleiro, A. Lévai and T. Patonay, J. Heterocycl. Chem., 1998, 35, 217.
11. The structure of 2,3-dibromo-2-(1,2-dibromo-2-phenylethyl)-4-chromanone (6d) is as follows: formula presented
12. 13C NMR resonances of isomers (Z)- and (E)-2-α-bromostyrylchromones (5) and (7): 5a-c, δ (ppm) 8.05-8.11 (H-β) and 133.9-135.2 (C-β); 7a-c, 7.41-7.46 (H-β) and 135.2-138.7 (C-β). Due to the non-coplanarity between the B ring and the other part of the molecule in the (E)-isomers (7a-c), H-β is shielded and C-β deshielded relatively to the (Z)-isomers (5a-c).
13. 13C NMR assignments.
14. 2: C , 70.58; H, 3.83; N, 14.53. Found: C, 70.71; H, 3.83; N, 14.30.
15. 2: C , 67.10; H, 3.97; N, 18.41. Found: C, 67.51; H, 4.25; N, 18.01.
16. S. J. Wittenberger, Org. Prep. Proced. Int., 1994, 26, 501.