A new domino-Knoevenagel-hetero-Diels-Alder reaction

Tetrahedron Letters

Volumn 49, Issue 31, 2008, Pages 4648-4651

  Matiychuk, Vasyl S ^a   Lesyk, Roman B ^b   Obushak, Mykola D ^a   Gzella, Andrzej ^c   Atamanyuk, Dmytro V ^b   Ostapiuk, Yuri V ^a   Kryshchyshyn, Anna P ^b  

^a IVAN FRANKO NATIONAL UNIVERSITY OF LVIV   (Ukraine)

^b DANYLO HALYTSKY LVIV NATIONAL MEDICAL UNIVERSITY   (Ukraine)

^c POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

2 ALLYLOXYBENZALDEHYDE; 3,5A,6,11B TETRAHYDRO 2H,5H CHROMENO[4',3':4,5]THIOPYRANO[2,3 D][1,3]THIAZOL 2 ONE; 4 THIOXO 1,3 THIAZOLIDIN 2 ONE; ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; CITRONELLAL; THIAZOLE DERIVATIVE; THIAZOLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; DOMINO KNOEVENAGEL HETERO DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

ALNUS;

EID: 45549086278     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.062     Document Type: Article

References (28)

1. Tietze L.F., Brasche G., and Gericke K. Domino Reactions in Organic Synthesis (2006), Wiley-VCH
2. Tietze L.F. Chem. Rev. 96 (1996) 115-136
3. Tietze L.F., and Rackelmann N. Pure Appl. Chem. 76 (2004) 1967-1983
4. Bogdanowicz-Szwed K., and Palasz A. Monatsh. Chem. 130 (1999) 795-807
5. Tietze L.F. J. Heterocycl. Chem. 27 (1990) 47-69
6. Snider B.B., and Lu Q. J. Org. Chem. 61 (1996) 2839-2844
7. Haake M., and Holz H. Phosphorus, Sulfur, Silicon Relat. Elem. 153 (1999) 407-408
8. Tietze L.F., Pfeiffer T., and Schuffenhauer A. Eur. J. Org. Chem. 12 (1998) 2733-2741
9. Davion Y., Joseph B., and Merour J.Y. Synlett (1998) 1051-1052
10. Sabitha G., Reddy E.V., Fatima N., Yadav J.S., Krishna K.V.S.R., and Kunwar A.C. Synthesis (2004) 1150-1154
11. Kassab N.A.E.L., Allah S.O.A., and Messeha N.A. J. Prakt. Chem. 316 (1974) 209-214
12. Ead H.A., Abdallah S.O., Kassab N.A., Metwalli N.H., and Saleh Y.E. Arch. Pharm. 320 (1987) 1227-1232
13. Metwally N.H. J. Sulfur Chem. 28 (2007) 275-284
14. Lesyk R., Zimenkovsky B., Atamanyuk D., Jensen F., Kiec-Kononowicz K., and Gzella A. Bioorg. Med. Chem. 14 (2006) 5230-5240
15. Lesyk R.B., and Zimenkovsky B.S. Curr. Org. Chem. 8 (2004) 1547-1577
16. Zimenkovsky B.S., Lukyanchuk V.D., Atamanyuk D.V., Renzyak S.Ya., and Lesyk R.B. Farm. Zh. (in Ukrainian) (2007) 78-88
17. Chem. Abstr. (2007) 836917
18. Preparation of (5aRS,8R,9aRS)-5,5,8-trimethyl-3,5,5a,6,7,8,9,9a-octahydro-2H-[2]benzoth iopyrano[3,4-d][1,3]thiazol-2-one (3). To a suspension of 10 mmol of 4-thioxo-2-thiazolidinone 1 in 10 ml of anhydrous acetonitrile, 13 mmol of citronellal 2 was added. Next, 5 mmol of EDDA in 10 ml of anhydrous acetonitrile was added under stirring. After 48 h, the reaction mixture was refluxed for 5 min and then cooled. The obtained precipitate was filtered off, washed with hexane and recrystallized from ethanol. Preparation of (5aRS,11bRS)-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4′,3′:4,5] thiopyrano[2,3-d][1,3]thiazol-2-one (5b). A solution of 2-allyloxybenzaldehyde 4 (10 mmol) and thiazolidinone 1 (10 mmol) in acetic acid or acetonitrile (20 ml) was stirred at room temperature in the presence of a catalytic amount of triethyamine (10 mmol). The progress of the reaction was monitored by TLC. The solid product that formed was collected by filtration and recrystallized from dioxane.
19. 2: C, 56.30; H, 4.00; N, 5.05. Found: C, 56.45; H, 4.15; N, 5.00.
20. 2): 0.032, 0.096. Crystallographic data for the structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 655431. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1233 336033 or e-mail deposit@ccdc.cam.ac.uk).
21. Cremer D., and Pople J.A. J. Am. Chem. Soc. 97 (1975) 1354-1358
22. 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
23. Typical procedure: A solution of appropriate unsaturated aldehyde (12 mmol), triethylamine (10 mmol) and 4-thioxo-2-thiazolidinone 1 (10 mmol) was stirred at room temperature in acetic acid (20 ml) for 12 h. The progress of the reaction was monitored by TLC. The solid product that formed was collected by filtration and recrystallized from ethanol.
24. +).
25. 50 = -4.27). These preliminary results are promising and need further investigation of the antitumor activity of reported and related compounds.
26. Monks A., Scudiero D., Skehan P., Shoemaker R., Paull K., Vistica D., Hose C., Langley J., Cronise P., and Vaigro-Wolff A. J. Nat. Cancer Inst. 83 (1991) 757-766
27. Boyd M.R., and Paull K.D. Drug Dev. Res. 34 (1995) 91-109
28. Monks A., Scudiero D.A., Johnson G.S., Paull K.D., and Sausville E.A. Anticancer Drug Des. 12 (1997) 533-541