Is samoquasine A indeed benzo[f]phthalazin-4(3H)-one? Unambiguous, straightforward synthesis of benzo[f]phthalazin-4(3H)-one and its regioisomer benzo[f]phthalazin-1(2H)-one

Tetrahedron

Volumn 63, Issue 18, 2007, Pages 3870-3881

  Monsieurs, Katrien ^a   Tapolcsányi, Pál ^b   Loones, Kristof T J ^a   Neumajer, Gábor ^b   Dirk De Ridder, J A ^c   Goubitz, Kees ^c   Lemière, Guy L F ^a   Dommisse, Roger A ^a   Mátyus, Péter ^b   Maes, Bert U W ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

^b SEMMELWEIS UNIVERSITY   (Hungary)

^c UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Benzophthalazine; Condensation; Natural product; Suzuki reaction

Indexed keywords

ALKALOID DERIVATIVE; ANNONA SQUAMOSA EXTRACT; BENZENE DERIVATIVE; BENZO[F]PHTHALAZIN 1(2H) ONE; BENZO[F]PHTHALAZIN 4(3H) ONE; CYTOTOXIC AGENT; NATURAL PRODUCT; PHTHALAZINE DERIVATIVE; PLANT EXTRACT; PYRIDAZINONE DERIVATIVE; SAMOQUASINE A; UNCLASSIFIED DRUG;

ANNONA SQUAMOSA; ARTICLE; CHEMICAL ANALYSIS; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FRUIT; ISOMER; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; SUZUKI REACTION;

ANNONA SQUAMOSA;

EID: 34047156501     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.031     Document Type: Article

References (30)

1. Morita H., Sato Y., Chan K.-L., Choo C.-Y., Itokawa H., Takeya K., and Kobayashi J. J. Nat. Prod. 63 (2000) 1707-1708 and references cited therein
2. Additions and corrections:. Morita H., Sato Y., Chan K.-L., Choo C.-Y., Itokawa H., Takeya K., and Kobayashi J. J. Nat. Prod. 65 (2002) 1748
3. 50 value of 0.38 μg/mL.
4. Yang Y.L., Chang F.R., and Wu Y.C. Tetrahedron Lett. 44 (2003) 319-322
5. Chakrabarty M., Sarkar S., and Harigaya Y. Synthesis (2003) 2292-2294
6. Mátyus P., Maes B.U.W., Riedl Z., Hajós G., Lemière G.L.F., Tapolcsányi P., Monsieurs K., Éliás O., Dommisse R.A., and Krajsovszky G. Synlett (2004) 1123-1139
7. For a review on Pd-catalyzed reactions on pyridazines including Suzuki reactions see:. Maes B.U.W., Tapolcsányi P., Meyers C., and Mátyus P. Curr. Org. Chem. 10 (2006) 377-417
8. Zára-Kaczián E., and Mátyus P. Heterocycles 36 (1993) 519-528
9. Riedl Z., Maes B.U.W., Monsieurs K., Lemière G.L.F., Mátyus P., and Hajós G. Tetrahedron 58 (2002) 5645-5650
10. Zou G., Reddy Y.K., and Falck J.R. Tetrahedron Lett. 42 (2001) 7213-7215
11. Zou G., and Falck J.R. Tetrahedron Lett. 42 (2001) 5817-5819
12. Molander G.A., and Yun C.S. Tetrahedron 58 (2002) 1465-1470
13. Molander G.A., and Yokoyama Y. J. Org. Chem. 71 (2006) 2493-2498
14. Molander G.A., Yun C.-S., Ribagorda M., and Biolatto B. J. Org. Chem. 68 (2003) 5534-5539
15. Christoforou I.C., Koutentis P.A., and Rees C.W. Org. Biomol. Chem. 1 (2003) 2900-2907
16. Gray M., Andrews I.P., Hook D.F., Kitteringham J., and Voyle M. Tetahedron Lett. 41 (2000) 6237-6240
17. Botella L., and Nájera C. Angew. Chem., Int. Ed. 41 (2002) 179-181
18. Botella L., and Nájera C. J. Organomet. Chem. 663 (2002) 47-57
19. Soderquist J.A., and Santiago B. Tetrahedron Lett. 31 (1990) 5541-5542
20. Jin B., Liu Q., and Sulikowski G.A. Tetrahedron 61 (2005) 401-408
21. Gronowitz S., Bobosik V., and Lawitz K. Chem. Scripta 23 (1984) 120-122
22. For an experimental set-up that allows an exact comparison of microwave and conventional heating (oil bath) see:. Hostyn S., Maes B.U.W., Van Baelen G., Gulevskaya A., Meyers C., and Smits K. Tetrahedron 62 (2006) 4676-4684
23. Stevenson T.M., Crouse B.A., Thieu T.V., Gebreysus C., Finkelstein B.L., Sethuraman M.R., Dubas-Cordery C.M., and Piotrowski D.L. J. Heterocycl. Chem. 42 (2005) 427-435
24. Maes B.U.W., Monsieurs K., Loones K.T.J., Lemière G.L.F., Dommisse R., Mátyus P., Riedl Z., and Hajós G. Tetrahedron 58 (2002) 9713-9721
25. Monsieurs K., Rombouts G., Tapolcsányi P., Mátyus P., and Maes B.U.W. Synlett (2006) 3225-3230
26. For the comparison of the heating efficiency of several commercially available microwave platforms see:. Loones K.T.J., Maes B.U.W., Rombouts G., Hostyn S., and Diels G. Tetrahedron 61 (2005) 10338-10348
27. Crystallographic data for the structure 3 in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-631245. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223 336 033 or e-mail: deposit@ccdc.cam.ac.uk).
28. Crystallographic data for the structure 17 in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-631398. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223 336 033 or e-mail: deposit@ccdc.cam.ac.uk).
29. Kobe J., Krbavčič A., Stanovnik B., and Tišler M. Croat. Chem. Acta 41 (1969) 245-250
30. Gagnier R.P., Halat M.J., and Otter B.A. J. Heterocycl. Chem. 21 (1984) 481-489