Toward safer methodologies for the synthesis of polyheterocyclic systems: Intramolecular arylation of arenes under Mizoroki-Heck reaction conditions

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1095-1098

  Hernández, Susana ^a   SanMartin, Raul ^a   Tellitu, Imanol ^a   Domínguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; CELECOXIB; HETEROCYCLIC COMPOUND; IBUDILAST; PHENANTHRIDINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ANION EXCHANGE; ARTICLE; ARYLATION; CYCLIZATION; DRUG SYNTHESIS; HECK REACTION; RING CLOSING METATHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0141742132     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034148+     Document Type: Article

References (58)

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30. For pyrazolo[1,5-a]pyridines as antiviral agents, see: (a) Gudmundsson, K.; Johns, B. A. (Smithkline Beecham Co.) WO0288124, 2002 (C. A. 137: 337887). (b) Alberti, M. J.; Chamberlain, S. D.; Chueng, M.; Gudmundsson, K.; Harris, P. A.; Johns, B. A.; Jung, D. K.; Peel, M. R.; Stanford, J. B. (Smithkline Beecham Co.) WO0278700, 2002 (Chem. Abstr. 2002, 137, 294953). Pyrazolopyridines, pyrazoloquinolines, and pyrazolo-isoquinolines are reported as dopamine D4 and adenosine A1-A2 receptor antagonists or amyloidosis modulating agents. See for example: (c) Akahane, A.; Tanaka, A.; Minagawa, M.; Itani, H.; Ohtake, H. (Fujisawa Pharmaceutical Co.) WO0218382, 2002 (Chem. Abstr. 2002, 136, 232298). (d) Reiner, P. B.; Lam, F. C.-L. US20020037843, 2002 (Chem. Abstr. 2002, 136, 257275). See also: (e) Bettinetti, L.; Schlotter, K.; Huebner, H.; Gmeiner, P. J. Med. Chem. 2002, 45, 4594-4597.
31. For pyrazolo[1,5-a]pyridines as antiviral agents, see: (a) Gudmundsson, K.; Johns, B. A. (Smithkline Beecham Co.) WO0288124, 2002 (C. A. 137: 337887). (b) Alberti, M. J.; Chamberlain, S. D.; Chueng, M.; Gudmundsson, K.; Harris, P. A.; Johns, B. A.; Jung, D. K.; Peel, M. R.; Stanford, J. B. (Smithkline Beecham Co.) WO0278700, 2002 (Chem. Abstr. 2002, 137, 294953). Pyrazolopyridines, pyrazoloquinolines, and pyrazolo-isoquinolines are reported as dopamine D4 and adenosine A1-A2 receptor antagonists or amyloidosis modulating agents. See for example: (c) Akahane, A.; Tanaka, A.; Minagawa, M.; Itani, H.; Ohtake, H. (Fujisawa Pharmaceutical Co.) WO0218382, 2002 (Chem. Abstr. 2002, 136, 232298). (d) Reiner, P. B.; Lam, F. C.-L. US20020037843, 2002 (Chem. Abstr. 2002, 136, 257275). See also: (e) Bettinetti, L.; Schlotter, K.; Huebner, H.; Gmeiner, P. J. Med. Chem. 2002, 45, 4594-4597.
32. For pyrazolo[1,5-a]pyridines as antiviral agents, see: (a) Gudmundsson, K.; Johns, B. A. (Smithkline Beecham Co.) WO0288124, 2002 (C. A. 137: 337887). (b) Alberti, M. J.; Chamberlain, S. D.; Chueng, M.; Gudmundsson, K.; Harris, P. A.; Johns, B. A.; Jung, D. K.; Peel, M. R.; Stanford, J. B. (Smithkline Beecham Co.) WO0278700, 2002 (Chem. Abstr. 2002, 137, 294953). Pyrazolopyridines, pyrazoloquinolines, and pyrazolo-isoquinolines are reported as dopamine D4 and adenosine A1-A2 receptor antagonists or amyloidosis modulating agents. See for example: (c) Akahane, A.; Tanaka, A.; Minagawa, M.; Itani, H.; Ohtake, H. (Fujisawa Pharmaceutical Co.) WO0218382, 2002 (Chem. Abstr. 2002, 136, 232298). (d) Reiner, P. B.; Lam, F. C.-L. US20020037843, 2002 (Chem. Abstr. 2002, 136, 257275). See also: (e) Bettinetti, L.; Schlotter, K.; Huebner, H.; Gmeiner, P. J. Med. Chem. 2002, 45, 4594-4597.
33. The strategy aminomethylenation/amine-exchange/heterocyclization has been previously exploited by our group. Although the mechanism of the tandem amine-exchange/heterocyclization is still unknown, several proposals have been made so far. See: (a) Domínguez, E.; Martínez de Marigorta, E.; Olivera, R.; SanMartin, R. Synlett 1995, 955-956. (b) Olivera, R.; SanMartin, R.; Domínguez, E.; Solans, X.; Urtiaga, M. K.; Arriortua, M. I. J. Org. Chem. 2000, 65, 6398-6411.
34. The strategy aminomethylenation/amine-exchange/heterocyclization has been previously exploited by our group. Although the mechanism of the tandem amine-exchange/heterocyclization is still unknown, several proposals have been made so far. See: (a) Domínguez, E.; Martínez de Marigorta, E.; Olivera, R.; SanMartin, R. Synlett 1995, 955-956. (b) Olivera, R.; SanMartin, R.; Domínguez, E.; Solans, X.; Urtiaga, M. K.; Arriortua, M. I. J. Org. Chem. 2000, 65, 6398-6411.
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50. 4Br (1.82 mmol), and diaryl pyrazole 4 (1.80 mmol) under argon at room temperature. After the tube was closed, it was heated to 110°C for 6-24 h until TLC showed the completion of the reaction. After cooling, the crude was poured onto an ice (5 g)/water (20 mL) mixture. The aqueous layer was extracted with diethyl ether (3 x 20 mL), and the combined organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to give a residue that was purified by flash chromatography on silicagel with 5-20% EtOAc/hexane as eluent.
51. Although no detailed mechanism for this type of arylation has been proposed so far, reductive elimination of palladacycle intermediates is usually assumed as the last step of the mechanistic pathway. See ref 2a for more details.
52. Normally such an aryl halide moiety is part of a benzamide or a benzoate framework. See, for example, refs 2c and 2d. See also: (a) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004-1015. (b) Kitamura, M.; Ohmori, K.; Kawase, T.; Suzuki, K. Angew. Chem., Int. Ed. 1999, 38, 1229-1232. (c) Harayama, T.; Akiyama, T.; Nakano, Y.; Shibaike, K.; Akamatsu, H.; Hori, A.; Abe, H.; Takeuchi, Y. Synthesis 2002, 237-241.
53. Normally such an aryl halide moiety is part of a benzamide or a benzoate framework. See, for example, refs 2c and 2d. See also: (a) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004-1015. (b) Kitamura, M.; Ohmori, K.; Kawase, T.; Suzuki, K. Angew. Chem., Int. Ed. 1999, 38, 1229-1232. (c) Harayama, T.; Akiyama, T.; Nakano, Y.; Shibaike, K.; Akamatsu, H.; Hori, A.; Abe, H.; Takeuchi, Y. Synthesis 2002, 237-241.
54. Normally such an aryl halide moiety is part of a benzamide or a benzoate framework. See, for example, refs 2c and 2d. See also: (a) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004-1015. (b) Kitamura, M.; Ohmori, K.; Kawase, T.; Suzuki, K. Angew. Chem., Int. Ed. 1999, 38, 1229-1232. (c) Harayama, T.; Akiyama, T.; Nakano, Y.; Shibaike, K.; Akamatsu, H.; Hori, A.; Abe, H.; Takeuchi, Y. Synthesis 2002, 237-241.
55. Further mechanistic discussions about the role of the pyrazole nucleus and possible chelating effects will be published elsewhere.
56. Celecoxib has been reported to be a selective cyclo-oxygenase-2 (COX-2) inhibitor, with remarkable antiinflammatory, analgesic, and antipyretic activities associated with a high degree of gastrointestinal safety. Other applications of this drug include the treatment of preterm labor, osteoarthritis and rheumatoid arthritis, inflammatory bowel disease, and duodenal polyposis in familial adenomatous polyposis, or preventing pain after otolaryngologic surgery. See: (a) Stika, C. S.; Gross, G. A.; Leguizamon, G.; Gerber, S.; Levy, R.; Mathur, A.; Bernhard, L. M.; Nelson, D. M.; Sadovsky, Y. Am. J. Obstet. Gynecol. 2002, 187, 653-660. (b) Dilger, K.; Herrlinger, C.; Peters, J.; Seyberth, H. W.; Schweer, H.; Klotz, U. J. Clin. Pharmacol. 2002, 42, 985-994. (c) Woessner, K. M.; Simon, R. A.; Stevenson, D. D. Arthritis Rheum. 2002, 46, 2201-2206.
57. Celecoxib has been reported to be a selective cyclo-oxygenase-2 (COX-2) inhibitor, with remarkable antiinflammatory, analgesic, and antipyretic activities associated with a high degree of gastrointestinal safety. Other applications of this drug include the treatment of preterm labor, osteoarthritis and rheumatoid arthritis, inflammatory bowel disease, and duodenal polyposis in familial adenomatous polyposis, or preventing pain after otolaryngologic surgery. See: (a) Stika, C. S.; Gross, G. A.; Leguizamon, G.; Gerber, S.; Levy, R.; Mathur, A.; Bernhard, L. M.; Nelson, D. M.; Sadovsky, Y. Am. J. Obstet. Gynecol. 2002, 187, 653-660. (b) Dilger, K.; Herrlinger, C.; Peters, J.; Seyberth, H. W.; Schweer, H.; Klotz, U. J. Clin. Pharmacol. 2002, 42, 985-994. (c) Woessner, K. M.; Simon, R. A.; Stevenson, D. D. Arthritis Rheum. 2002, 46, 2201-2206.
58. Celecoxib has been reported to be a selective cyclo-oxygenase-2 (COX-2) inhibitor, with remarkable antiinflammatory, analgesic, and antipyretic activities associated with a high degree of gastrointestinal safety. Other applications of this drug include the treatment of preterm labor, osteoarthritis and rheumatoid arthritis, inflammatory bowel disease, and duodenal polyposis in familial adenomatous polyposis, or preventing pain after otolaryngologic surgery. See: (a) Stika, C. S.; Gross, G. A.; Leguizamon, G.; Gerber, S.; Levy, R.; Mathur, A.; Bernhard, L. M.; Nelson, D. M.; Sadovsky, Y. Am. J. Obstet. Gynecol. 2002, 187, 653-660. (b) Dilger, K.; Herrlinger, C.; Peters, J.; Seyberth, H. W.; Schweer, H.; Klotz, U. J. Clin. Pharmacol. 2002, 42, 985-994. (c) Woessner, K. M.; Simon, R. A.; Stevenson, D. D. Arthritis Rheum. 2002, 46, 2201-2206.