New pathways towards pyridazino-fused ring systems

Synlett

Volumn , Issue 7, 2004, Pages 1123-1139

  Mátyus, Péter ^{a,d,e,f,g,h,i,j,k,l,m}   Maes, Bert U W ^a,b,g,n,o   Riedl, Zsuzsanna ^{c,g,p,q,r,s,t}   Hajós, György ^c   Lemière, Guy L F ^b   Tapolcsányi, Pál ^a   Monsieurs, Katrien ^b   Éliás, Olivér ^a   Dommisse, Roger A ^b   Krajsovszky, Gábor ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b UNIVERSITY OF ANTWERP   (Belgium)

^c CHEMICAL RESEARCH CENTER   (Hungary)

^d BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^e Institute for Drug Research Budapest   (Hungary)

^f Technical University   (Hungary)

^g INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^h Department of Pharmacodynamics and Biopharmacy Faculty of Pharmacy   (Hungary)

ⁱ UNIVERSITY OF BONN   (Germany)

^j KYOTO UNIVERSITY   (Japan)

^k Fuji's Department   (Hungary)

^l AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^m Garibaldi U 2   (Hungary)

ⁿ RESEARCH FOUNDATION FLANDERS FWO   (Belgium)

^o Rosa Blanckaert' Foundation   (Italy)

^p EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^q Rosa Blanckaert' Foundation ^*  (Hungary)

^r Instrumental Organ Analyt Chem L   (Hungary)

^s UNIVERSITY OF GRAZ   (Austria)

^t Kisfaludy Lajos' Foundation   (Hungary)

more..

Author keywords

Diazino fused ring systems; Palladium catalyzed reaction; Pyridazine; Pyridazino fused ring systems

Indexed keywords

2 BENZYL 1H ISOCHROMENO[3,4 D]PYRIDAZIN 1,6(2H) DIONE; 2 DIAZINOPHENYLPYRIDAZINONE; 2 METHYL 4,5 DIPHENOXYPYRIDAZIN 3(2H) ONE; 2 METHYL 5 IODOPYRIDAZIN 3(2H) ONE; 2 METHYLBENZO[B]FURO[2,3 D]PYRIDAZIN 1(2H) ONE; 3 BENZYL 3H ISOCHROMENO[3,4 D]PYRIDAZIN 4,6 DIONE; 3 METHYLPYRIDAZINO[4,5 B]INDOL 4(3H) ONE; 4 BROMO 2 METHYL 5 PHENOXYPYRIDAZIN 3(2H) ONE; 4 CHLORO 2 METHYL 5 PHENOXYPYRIDAZIN 3(2H) ONE; 4 CHLORO 5 METHOXY 2 METHYLPYRIDAZIN 3(2H) ONE; 4 CHLORO 5 METHOXYPYRIDAZINONE; 4,5 DIBROMO 2 METHYLPYRIDAZIN 3(2H) ONE; 4,5 DICHLORO 2 METHYLPYRIDAZIN 3(2H) ONE; 4,5 DICHLOROPYRIDAZINE; 5 (2 BROMOPHENYL) 4 PHENYLPYRIDAZINONE; 5 AMINO 6 CHLORO 1,3 DIMETHYLPYRIMIDINE 2,4(1H, 3H) DIONE; 5 AMINO 6 CHLORO 2,4(1H, 3H) PYRIMIDINEDIONE; 5 IODO 2 METHYL 3(2H) PYRIDAZINONE; 5 METHOXY 4 PHENYLPYRIDAZINONE; 5(4) CHLORO 4(5) METHOXYPYRIDAZINE; 6 CHLORO 1,3 DIMETHYLPYRIMIDINE 2,4(1H, 3H) DIONE; BENZENE DERIVATIVE; CHLOROMETHOXYPYRIDAZIN 3(2H) ONE; CHLOROMETHOXYPYRIDAZINE; METHOXYPYRIDAZIN 3(2H) ONE; PYRAZINO[1,2 B]INDAZOLE; PYRIDAZINE DERIVATIVE; PYRIDAZINONE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; ARYLATION; DRUG SCREENING; DRUG SYNTHESIS; HECK REACTION; LACTONIZATION; POLYMERIZATION; SEQUENTIAL ANALYSIS; SUZUKI REACTION;

EID: 2942700383     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822894     Document Type: Article

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51. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
52. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
53. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
54. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
55. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
56. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
57. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
58. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
59. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
60. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
61. Examples of Pd-catalyzed intramolecular arylation: (a) Rice, J. E.; Cai, Z. W. Tetrahedron Lett. 1992, 33, 1675. (b) Rice, J. E.; Cai, Z. W. J. Org. Chem. 1993, 58, 1415. (c) Hennings, D. D.; Iwasa, S.; Rawal, V. H. Tetrahedron Lett. 1997, 38, 6379. (d) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (e) Gonzalez, J. J.; Garcia, N.; Gómez Lor, B.; Echavarren, A. M. J. Org. Chem. 1997, 62, 1286. (f) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525. (g) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427. (h) Wang, L.; Shelvin, P. B. Org. Lett. 2000, 2, 3703. (i) Marcinov, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett 2001, 3, 3527. (j) Mehta, G.; Sarma, P. V. V. S. Tetrahedron Lett. 2002, 43, 6557. (k) Echavarren, A. M.; Gómez, J. J.; de Frutos, Ó. Synlett 2003, 585. (l) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
62. Tapolcsányi, P.; Maes, B. U. W.; Monsieurs, K.; Lemière, G. L. F.; Riedl, Z.; Hajós, G.; Van den Driessche, B.; Dommisse, R. A.; Mátyus, P. Tetrahedron 2003, 59, 5919.
63. Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287.
64. Smith, B. M.; March, J. Advanced Organic Chemistry, 5th ed.; Wiley-Interscience: New York, 2000, Chap. 14.17, 928-929.
65. For a review for transformations of aryldiazonium salts see: Galli, C. Chem. Rev. 1988, 88, 765.
66. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
67. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
68. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
69. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
70. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
71. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
72. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
73. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
74. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
75. For examples of intramolecular Heck-type reactions for the construction of carbazole carboline and dibenzofurane skeletons and their aza-analogues see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938. (b) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383. (c) Ames, D. E.; Opalko, A. Synthesis 1983, 234. (d) Chen, C. Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676. (e) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505. (f) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (g) Zhang, Y. M.; Razler, T.; Jackson, P. F. Tetrahedron Lett. 2002, 43, 8235. (h) Bedford, R. B.; Cazin, C. S. J. Chem. Commun. 2002, 2310. (i) Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Rombouts, G.; Pieters, L.; Haemers, A.; Dommisse, R. A. Synlett 2003, 615. (j) Ferreira, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737.
76. Dajka-Halász, B.; Monsieurs, K.; Éliás, O.; Károlyházy, L.; Tapolcsányi, P.; Maes, B. U. W.; Riedl, Z.; Hajós, G.; Dommisse, R. A.; Lemière, G. L. F.; Košmrlj, J.; Mátyus, P. Tetrahedron 2004, 60, 2283.
77. 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: (a) Kang, Y. J.; Chung, H. A.; Kweon, D. H.; Cho, S. D.; Lee, S. G.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 595. (b) Kweon, D. H.; Kang, Y. J.; Chung, H. A.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 819. (c) Kweon, D. H.; Chung, J. W.; Cho, S. D.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 1401. (d) Chung, H. A.; Kim, J. J.; Cho, S. D.; Lee, S. G.; Yoon, Y. J. J. Heterocycl. Chem. 2002, 39, 685.
78. 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: (a) Kang, Y. J.; Chung, H. A.; Kweon, D. H.; Cho, S. D.; Lee, S. G.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 595. (b) Kweon, D. H.; Kang, Y. J.; Chung, H. A.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 819. (c) Kweon, D. H.; Chung, J. W.; Cho, S. D.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 1401. (d) Chung, H. A.; Kim, J. J.; Cho, S. D.; Lee, S. G.; Yoon, Y. J. J. Heterocycl. Chem. 2002, 39, 685.
79. 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: (a) Kang, Y. J.; Chung, H. A.; Kweon, D. H.; Cho, S. D.; Lee, S. G.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 595. (b) Kweon, D. H.; Kang, Y. J.; Chung, H. A.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 819. (c) Kweon, D. H.; Chung, J. W.; Cho, S. D.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 1401. (d) Chung, H. A.; Kim, J. J.; Cho, S. D.; Lee, S. G.; Yoon, Y. J. J. Heterocycl. Chem. 2002, 39, 685.
80. 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: (a) Kang, Y. J.; Chung, H. A.; Kweon, D. H.; Cho, S. D.; Lee, S. G.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 595. (b) Kweon, D. H.; Kang, Y. J.; Chung, H. A.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 819. (c) Kweon, D. H.; Chung, J. W.; Cho, S. D.; Kim, S. K.; Yoon, Y. J. J. Heterocycl. Chem. 1998, 35, 1401. (d) Chung, H. A.; Kim, J. J.; Cho, S. D.; Lee, S. G.; Yoon, Y. J. J. Heterocycl. Chem. 2002, 39, 685.
81. 4NY in DMF' are the 'Jefferey's' reaction conditions. For intermolecular Heck reactions under 'Jefferey's' conditions see: Jefferey, T. Tetrahedron 1996, 52, 10113.
82. For reviews on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2047. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (e) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000, 195-262. (f) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (g) For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (h) See also: Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
83. For reviews on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2047. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (e) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000, 195-262. (f) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (g) For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (h) See also: Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
84. For reviews on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2047. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (e) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000, 195-262. (f) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (g) For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (h) See also: Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
85. For reviews on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2047. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (e) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000, 195-262. (f) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (g) For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (h) See also: Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
86. For reviews on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2047. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (e) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000, 195-262. (f) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (g) For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (h) See also: Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
87. For reviews on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2047. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (e) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000, 195-262. (f) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (g) For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (h) See also: Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
88. For reviews on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2047. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (e) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000, 195-262. (f) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (g) For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (h) See also: Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
89. For reviews on the Buchwald-Hartwig reaction see: (a) Barañano, D.; Mann, G.; Hartwig, J. F. Curr. Org. Chem. 1997, 1, 287. (b) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615. (c) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2047. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (e) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000, 195-262. (f) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (g) For recent reviews containing a chapter on the Buchwald-Hartwig reaction see: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176. (h) See also: Prim, D.; Campagne, J. M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
90. Košmrlj, J.; Maes, B. U. W.; Lemière, G. L. F.; Haemers, A. Synlett 2000, 1581.
91. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.
92. Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359.
93. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066.
94. (a) Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481.
95. (b) For other examples dealing with the rate accelerating effect of large excesses of carbonate bases on Pd-catalyzed aminations see: Jonckers, T. H. M.; Maes, B. U. W.; Lemière, G. L. F.; Dommisse, R. Tetrahedron 2001, 57, 7027.
96. (c) And: Maes, B. U. W.; Loones, K. T. J.; Jonckers, T. H. M.; Lemière, G. L. F.; Dommisse, R. A.; Haemers, A. Synlett 2002, 1995.