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For benzo[b]furo[2,3-d]pyridazines see: (l)
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For benzo[b]furo[2,3-d]pyridazines see: (l) Nagai S., Ueda T., Sakakibara H., Nagatsu A., Murakami N., Sakakibara J. J. Heterocycl. Chem. 35:1998;591-594.
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Riedl Z., Maes B.U.W., Monsieurs K., Lemière G.L.F., Mátyus P., Hajós G. Tetrahedron. 58:2002;5645-5650.
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Maes B.U.W., Monsieurs K., Loones K., Lemière G.L.F., Dommisse R., Mátyus P., Riedl Z., Hajós G. Tetrahedron. 58:2002;9713-9721.
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Tapolcsányi P., Krajsovszky G., Andó R., Lipcsey P., Horváth G., Mátyus P., Riedl Z., Hajós G., Maes B.U.W., Lemière G.L.F. Tetrahedron. 58:2002;10137-10143.
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25344449153
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For the synthesis of 5H-pyridazino[4,5-b]indoles via the reaction of a 2,3-dicarbonylated indole with a hydrazine see: (a). R.N. Castle. Wiley-Interscience
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For the synthesis of 5H-pyridazino[4,5-b]indoles via the reaction of a 2,3-dicarbonylated indole with a hydrazine see: (a) Tišler M., Stanovnik B. Castle R.N. Condensed pyridazines including cinnolines and phthalazines. 1973;766-800 Wiley-Interscience.
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Tišler, M.1
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84987367502
-
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For the synthesis of benzo[b]furo[2,3-d]pyridazines via the reaction of a 2,3-dicarbonylated benzo[b]furane with a hydrazine see: (d)
-
For the synthesis of benzo[b]furo[2,3-d]pyridazines via the reaction of a 2,3-dicarbonylated benzo[b]furane with a hydrazine see: (d) Cugnon de Sevricourt M., Robba M. J. Heterocycl. Chem. 14:1977;777-780.
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85030903083
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See Ref. 3a.
-
See Ref. 3a.
-
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34
-
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0001304357
-
-
For the use of an intramolecular Heck-type reaction for the construction of carbazole, carboline and dibenzofurane skeletons and their aza-analogues see: (a)
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For the use of an intramolecular Heck-type reaction for the construction of carbazole, carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida H., Yuasa Y., Kibayashi C. J. Org. Chem. 45:1980;2938-2942.
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0000324324
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For a recent review dealing with direct arylation via cleavage of activated and unactivated C-H bonds see:
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For a recent review dealing with direct arylation via cleavage of activated and unactivated C-H bonds see: Miura M., Nomura M. Top. Curr. Chem. 219:2002;211-241.
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3743113417
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For reviews on the Buchwald-Hartwig reaction see: (a)
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For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: (g)
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For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: (g) Littke A.F., Fu G.C. Angew. Chem. Int. Ed. 41:2002;4176-4211.
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For the synthesis of 2-substituted 5-alkoxy-4-halopyridazin-3(2H)-ones via selective alkanolysis of 2-substituted 4,5-dihalopyridazin-3(2H)-ones see: (a)
-
For the synthesis of 2-substituted 5-alkoxy-4-halopyridazin-3(2H)-ones via selective alkanolysis of 2-substituted 4,5-dihalopyridazin-3(2H)-ones see: (a) Barlin G.B., Lakshminarayanan P. J. Chem. Soc., Perkin Trans. 1. 1977;1038-1044.
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58
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0000223756
-
-
For the synthesis of 2-substituted 5-aryloxy-4-halopyridazin-3(2H)-ones via phenolysis of 2-substituted 4,5-dihalopyridazin-3(2H)-ones see: (f)
-
For the synthesis of 2-substituted 5-aryloxy-4-halopyridazin-3(2H)-ones via phenolysis of 2-substituted 4,5-dihalopyridazin-3(2H)-ones see: (f) Kang Y.-J., Chung H.-A., Kweon D.-H., Cho S.-D., Lee S.-G., Kim S.-K., Yoon Y.-J. J. Heterocycl. Chem. 35:1998;595-600.
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62
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0001314470
-
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For general reviews dealing with the synthesis of 2-substituted 4,5-dihalopyridazin-3(2H)-ones and the regioselective nucleophilic substitution of the addition-elimination type on these substrates with O, S and N nucleophiles see: (j)
-
For general reviews dealing with the synthesis of 2-substituted 4,5-dihalopyridazin-3(2H)-ones and the regioselective nucleophilic substitution of the addition-elimination type on these substrates with O, S and N nucleophiles see: (j) Mátyus P., Czakó K. Trends Heterocycl. Chem. 3:1993;249-264.
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Mátyus, P.1
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64
-
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84986528197
-
-
Identification of the 4-halo-2-methyl-5-phenoxypyridazin-3(2H)-one (
-
5,6 values on mono-substituted pyridazin-3(2H)-ones see: (a) Katz D.Z., Wise D.S., Townsend L.B. J. Heterocycl. Chem. 20:1983;369-379.
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Katz, D.Z.1
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Townsend, L.B.3
-
65
-
-
85030903843
-
-
See Ref. 9g.
-
See Ref. 9g.
-
-
-
-
66
-
-
85030902387
-
-
For the related alkanolysis of 4,5-dichloropyridazin-3(2H)-ones with sodium alkanolates in acetonitrile at room temperature a mixture of two alkoxy-chloropyridazin-3(2H)-one isomers was also obtained: see Ref. 9b
-
For the related alkanolysis of 4,5-dichloropyridazin-3(2H)-ones with sodium alkanolates in acetonitrile at room temperature a mixture of two alkoxy-chloropyridazin-3(2H)-one isomers was also obtained: see Ref. 9b.
-
-
-
-
68
-
-
0000907059
-
-
3 and NaOAc in DMA are the Spencer's reaction conditions. For intermolecular Heck reactions under 'Spencer's' conditions see: (a)
-
3 and NaOAc in DMA are the Spencer's reaction conditions. For intermolecular Heck reactions under 'Spencer's' conditions see: (a) Spencer A. J. Organomet. Chem. 258:1983;101-108.
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Spencer, A.1
-
70
-
-
85030909305
-
-
note
-
The most important side reaction observed in the Pd-catalyzed cyclodehydrohalogenation of 8a and 8b is hydrodehalogenation. The formation of 2-methyl-5-phenoxypyridazin-3(2H)-one has been proven by NMR analysis of the column chromatography fractions that revealed the presence of a compound with a molecular mass of 202.
-
-
-
-
71
-
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50849151376
-
-
2 or Pd(BINAP) catalyst is ArI>ArBr≫ArCl. However, the presence of electron withdrawing groups on, as well as the incorporation of nitrogen atoms in the benzene ring of the aryl chloride makes oxidative addition of aryl chlorides to palladium catalysts with traditional triarylphosphane ligands possible: (a)
-
2 or Pd(BINAP) catalyst is ArI>ArBr≫ArCl. However, the presence of electron withdrawing groups on, as well as the incorporation of nitrogen atoms in the benzene ring of the aryl chloride makes oxidative addition of aryl chlorides to palladium catalysts with traditional triarylphosphane ligands possible: (a) Fitton P., Rick E.A. J. Organomet. Chem. 28:1971;287-291.
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Fitton, P.1
Rick, E.A.2
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72
-
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85030913993
-
-
See Ref. 8g.
-
See Ref. 8g.
-
-
-
-
73
-
-
85030893822
-
-
note
-
4NBr (1 equiv.): no reaction.
-
-
-
-
74
-
-
0030598098
-
-
4NY in DMF are the Jefferey's reaction conditions. For intermolecular Heck reactions under Jefferey's conditions see:
-
4NY in DMF are the Jefferey's reaction conditions. For intermolecular Heck reactions under Jefferey's conditions see: Jefferey T. Tetrahedron. 52:1996;10113-10130.
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(1996)
Tetrahedron
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-
-
Jefferey, T.1
-
75
-
-
0000137450
-
-
For the effect of halide anions on Pd-catalyzed reactions see: (a)
-
For the effect of halide anions on Pd-catalyzed reactions see: (a) Amatore C., Azzabi M., Jutand A. J. Am. Chem. Soc. 113:1991;8375-8384.
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-
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Amatore, C.1
Azzabi, M.2
Jutand, A.3
-
78
-
-
85030899808
-
-
It is often considered that the Pd-catalyzed cyclodehydrohalogenation involving C-H bond activation, occurs via the intramolecular electrophilic attack of the oxidative addition complex on the π system: (a) See Ref. 8.
-
It is often considered that the Pd-catalyzed cyclodehydrohalogenation involving C-H bond activation, occurs via the intramolecular electrophilic attack of the oxidative addition complex on the π system: (a) See Ref. 8.
-
-
-
-
79
-
-
0037266893
-
-
If one accepts this model the Pd-catalyzed cyclodehydrohalogenation involving the cleavage of a vinylic C-H bond (e.g., in
-
Echavarren A.M., Gómez-Lor B., González J.J., de Frutos Ó. Synlett. 2003;585-597. If one accepts this model the Pd-catalyzed cyclodehydrohalogenation involving the cleavage of a vinylic C-H bond (e.g., in 10 ) should occur more readily than when an aromatic C-H bond is involved (e.g., in 8 ) since the mechanistic pathway does not include loss of aromaticity. This is in accordance with the results we obtained when comparing the Pd-catalyzed cyclization of 8a with 10.
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(2003)
Synlett
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Echavarren, A.M.1
Gómez-Lor, B.2
González, J.J.3
De Frutos, Ó.4
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81
-
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0034700880
-
-
For publications dealing with the rate accelerating effect of large excesses of carbonate bases on Pd-catalyzed aminations see: (a)
-
For publications dealing with the rate accelerating effect of large excesses of carbonate bases on Pd-catalyzed aminations see: (a) Watanabe M., Nishiyama M., Yamamoto T., Koie Y. Tetrahedron Lett. 41:2000;481-483.
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Watanabe, M.1
Nishiyama, M.2
Yamamoto, T.3
Koie, Y.4
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84
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0036454157
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Maes B.U.W., Loones K.T.J., Jonckers T.H.M., Lemière G.L.F., Dommisse R.A., Haemers A. Synlett. 2002;1995-1998.
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Maes, B.U.W.1
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Dommisse, R.A.5
Haemers, A.6
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85
-
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85030908469
-
-
note
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3 were used 40% of 5-[(2-bromophenyl)amino]-2-methylpyridazin-3(2H)-one ( 15 ) and a recovery of 52% of 5-iodo-2-methylpyridazin-3(2H)-one ( 1 ) were obtained after refluxing for 3 h, whereas the use of 1 equiv. of the same base under the same reaction conditions gave a yield of 30% of 15 and a recovery of 63% of 1 in the same reaction time.
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86
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0347928722
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A similar selective behaviour has recently been reported by us for the Suzuki reaction of
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A similar selective behaviour has recently been reported by us for the Suzuki reaction of 11 with 2-bromophenylboronic acid. In this case the conjugate base of 2-bromophenylboronic acid probably sterically and electronically retards oxidative addition of the ortho C-Br bond to the Pd(0) catalyst: see Ref. 2e. Interestingly, also Armin de Meijere's group reported selectivity when using 2-bromophenylboronic acid in the Suzuki cross-coupling reaction with 1-bromonaphthalene: Wegner H.A., Scott L.T., de Meijere A. J. Org. Chem. 68:2003;883-887.
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(2003)
J. Org. Chem.
, vol.68
, pp. 883-887
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Wegner, H.A.1
Scott, L.T.2
De Meijere, A.3
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