Investigation of the regioselectivity of the Hurde-Mori reaction for the formation of bicyclic1,2,3-thiadiazoles

Tetrahedron

Volumn 66, Issue 29, 2010, Pages 5472-5478

  Turner, Martin ^a   Linder, Thomas ^a   Schnürch, Michael ^a   Mihovilovic, Marko D ^a   Stanetty, Peter ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

Annelated heterocycle; Cyclization; Protecting group; Regioselectivity; Systemic acquired resistance

Indexed keywords

1 TERT BUTYL 2 METHYL 5 THIOXOPYRROLIDINE 1,2 DICARBOXYLATE; 1 TERT BUTYL 3 METHYL 5 THIOXOPYRROLIDINE 1,3 DICARBOXYLATE; 1 TERT BUTYL 3 METHYL 5 [2 (ETHOXYCARBONYL)HYDRAZONO]PYRROLIDINE 1,3 DICARBOXYLATE; 4 TERT BUTYL 5 METHYL 5 4H PYRROLO[2,3 D][1,2,3]THIADIAZOLE 4,5 DICARBOXYLATE; 4 TERT BUTYL 6 METHYL 4H PYRROLO[2,3 D][1,2,3]THIADIAZOLE 4,6 DICARBOXYLATE; 4 TERT BUTYL 6 METHYL 4H PYRROLO[3,2 D][1,2,3]THIADIAZOLE 4,6 DICARBOXYLATE; 4H PYRROLO[2,3 D][1,2,3]THIADIAZOLE; 5,6 DIHYDRO 4H CYCLOPENTA[D][1,2,3]THIADIAZOLE 5 CARBONITRILE; 5,6 DIHYDRO 4H CYCLOPENTA[D][1,2,3]THIAZOLE DERIVATIVE; BICYCLIC 1,2,3 THIADIAZOLE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIMETHYL 4H PYRROLO[3,4 D][1,2,3]THIADIAZOLE 5,6(6H) DICARBOXYLATE; DIMETHYL 5H PYRROLO[3,4 D][1,2,3]THIADIAZOLE 5,6 DICARBOXYLATE; METHYL 2 THIOXOPYRROLIDINE 1 CARBOXYLATE; METHYL 2 [2 (ETHOXYCARBONYL)HYDRAZONO]PYRROLIDINE 1 CARBOXYLATE; METHYL 4H PYRROLO[2,3 D][1,2,3]THIADIAZOLE 4 CARBOXYLATE; METHYL 4H PYRROLO[2,3 D][1,2,3]THIADIAZOLE 5 CARBOXYLATE; METHYL 4H PYRROLO[2,3 D][1,2,3]THIADIAZOLE 6 CARBOXYLATE; METHYL 4H PYRROLO[3,2 D][1,2,3]THIADIAZOLE 6 CARBOXYLATE; METHYL 5,6 DIHYDRO 4H CYCLOPENTA[D][1,2,3]THIADIAZOLE 4 CARBOXYLATE; METHYL 5,6 DIHYDRO 4H CYCLOPENTA[D][1,2,3]THIADIAZOLE 5 CARBOXYLATE; METHYL 5H PYRROLO[3,4 D][1,2,3]THIADIAZOLE 6 CARBOXYLATE; PYRROLO[D][1,2,3]THIADIAZOLE CARBOXYLATE DERIVATIVE; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HURD MORI REACTION; PRIORITY JOURNAL; SYNTHESIS;

THIA;

EID: 77954315815     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.017     Document Type: Article

References (37)

1. Wu, M.; Sun, Q.; Yang, C.; Chen, D.; Ding, J.; Chen, Y.; Lin, L.; Xie, Y.Bioorg.Med.Chem.Lett.2007, 17, 869;
2. Gopalakrishnan, M.; Thanusu, J.; Kanagarajan, V.Med.Chem.Res.2007, 16, 392;
3. Cikotiene, I.; Kazlauskas, E.; Matuliene, J.; Michailoviene, V.; Torresan, J.; Jachno, J.; Matulis, D.Bioorg.Med.Chem.Lett.2009, 19, 1089.
4. Schurter, R.; Kunz, W.; Nyfelter, R.Eur.Pat.Appl.EP 313512A2, 1989.
5. Kunz, W.; Schurter, R.; Maetzke, T.Pestic.Sci.1997, 50, 275.
6. Walters, D.; Heil, M.Physiol.Mol.Plant Pathol.2007, 71, 3;
7. Yasuda, M.J.Pestic.Sci.2007, 32, 281;
8. Vlot, A.C.; Klessig, D.F.; Park, S.-W.Curr.Opin.Plant Biol.2008, 11, 436;
9. Walters, D.R.; Fountaine, J.M.J.Agric.Sci.2009, 147, 523;
10. Shah, J.Curr.Opin.Plant Biol.2009, 12, 459.
11. Stanetty, P.; Kunz, W.Eur.Pat.Appl.EP 780394A1, 1997.
12. Bakulev, V.A.; Dehaen, W.The Chemistry of 1,2,3-Thiadiazoles; John Wiley & Sons: New York, NY, 2004.
13. Pechmann, H.; Nold, A.Chem.Ber.1986, 28, 2588;
14. Martin, D.; Mucke, W.Liebigs Ann.Chem.1965, 6823, 90
15. Wolff, L.Liebigs Ann.Chem.1902, 325, 129;
16. Wolff, L.Liebigs Ann.Chem.1904, 333, 1.
17. Hurd, C.D.; Mori, R.I.J.Am.Chem.Soc.1955, 77, 5359; See also:
18. Demaree, P.; Doria, M.C.; Muchowsky, J.M.Can.J.Chem.1977, 55, 243;
19. Bellesia, F.; Grandi, R.; Pagnoni, U.; Treve, R.Gazz.Chim.Ital.1981, 11, 289;
20. Stanetty, P.; Turner, M.; Mihovilovic, M.D.In Targets in Heterocyclic Systems
21. Attanasi, O.A., Spinelli, D., Eds.; Società Chimica Italiana: Rome, 1999; Vol.3, pp 265-299.
22. Liu, Z.; Mu, Y.; Lin, J.; Chen, Y.Synth.Commun.2008, 38, 4407.
23. Fujita, M.; Nimura, K.; Kobori, T.; Hiyama, T.; Kondo, K.Heterocycles 1995, 41, 2413.
24. Fujita, M.; Kobori, T.; Hiyama, T.; Kondo, K.Heterocycles 1993, 36, 33.
25. L'abbé, G.; Vossen, P.; Dehaen, W.; Toppet, S.J.Chem.Soc., Perkin Trans.1 1995, 2079.
26. Zimmer, O.; Meier, H.Chem.Ber.1981, 114, 2938.
27. Hanold, N.; Kalbitz, H.; Zimmer, O.; Meier, H.Liebigs Ann.Chem.1986, 1344.
28. Stanetty, P.; Kremslehner, M.; Vo€lleke, H.J.Chem.Soc., Perkin Trans.1 1998, 853.
29. Stanetty, P.; Kremslehner, M.Heterocycles 1998, 48, 259.
30. Stanetty, P.; Turner, M.; Mihovilovic, M.D.Molecules 2005, 10, 367.
31. Yamamoto, J.; Imagawa, M.; Yamauchi, S.; Nakazawa, O.; Umezu, M.; Matsuura, T.Tetrahedron 1981, 37, 1871.
32. Gillard, A.-C.; Fabis, F.; Jolivet-Fouchet, S.; Rault, S.Tetrahedron Lett.1997, 38, 2271.
33. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W.D.Tetrahedron 1997, 53, 12789.
34. Guillena, G.; Nájera, C.; Ramón, D.J.Tetrahedron: Asymmetry 2007, 18, 2249.
35. New, J.S.; Yevich, J.P.J.Heterocycl.Chem.1984, 21, 1355.
36. Gross, K.; Bertini, M.; Jun, Y.M.; Beak, P.J.Org.Chem.1997, 62, 7679.
37. Braun, H.P.; Meier, H.Tetrahedron 1975, 31, 637.