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Volumn 65, Issue 26, 2009, Pages 5062-5073

Synthesis of 1,3-diarylated imidazo[1,5-a]pyridines with a combinatorial approach: metal-catalyzed cross-coupling reactions of 1-halo-3-arylimidazo[1,5-a]pyridines with arylmetal reagents

Author keywords

Cross coupling; Fluorescence; Halogenation; Imidazo 1,5 a pyridine

Indexed keywords

1 (2 THIENYL) 3 (4 FLUOROPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (2 THIENYL) 3 (4 METHOXYPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (2 THIENYL) 3 (4 TRIFLUOROMETHYLPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (2 THIENYL) 3 PHENYLIMIDAZO[1,5 A] PYRIDINE; 1 (3 METHOXYCARBONYLPHENYL) 3 PHENYLIMIDAZO [1,5 A] PYRIDINE; 1 (4 FLUOROPHENYL) 1 PHENYLIMIDAZO[1,5 A] PYRIDINE; 1 (4 FLUOROPHENYL) 3 (4 METHOXYPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (4 FLUOROPHENYL) 3 (4 TRIFLUOROMETHYLPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (4 METHOXYCARBONYLPHENYL) 3 PHENYLIMIDAZO [1,5 A] PYRIDINE; 1 (4 METHOXYPHENYL) 3 (4 FLUOROPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (4 METHOXYPHENYL) 3 (4 METHOXYPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (4 METHOXYPHENYL) 3 (4 TRIFLUOROMETHYLPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (4 METHOXYPHENYL) 3 PHENYLIMIDAZO[1,5 A] PYRIDINE; 1 (4 METHYLPHENYL) 3 (4 FLUOROPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (4 METHYLPHENYL) 3 (4 METHOXYPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (4 METHYLPHENYL) 3 (4 TRIFLUOROMETHYLPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 (4 METHYLPHENYL) 3 PHENYLIMIDAZO[1,5 A] PYRIDINE; 1 [4 (N,N DIMETHYLAMINO)PHENYL] 3 (4 TRIFLUOROMETHYLPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 PHENYL 3 (4 FLUOROPHENYL) 2 AZAINDOLIZINE; 1 PHENYL 3 (4 METHOXYPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 PHENYL 3 (4 TRIFLUOROMETHYLPHENYL)IMIDAZO[1,5 A] PYRIDINE; 1 PHENYL 3 PHENYLIMIDAZO[1,5 A] PYRIDINE; 1(4 FLUOROPHENYL) 3 (4 FLUOROPHENYL)IMIDAZO[1,5 A] PYRIDINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 65749105973     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.062     Document Type: Article
Times cited : (78)

References (54)
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    • In the electrophilic substitution of imidazo[1,5-a]pyridines with acetyl chloride, the course of the reaction is entirely different from usual electrophilic substitution. The imidazole nitrogen atom first attacks the electrophile. Next, the intermediate salt is deprotonated at the C1 (or C3) position. Finally, migration of the electrophile to this position gives the product. Therefore, Lewis acid or base additive may inhibit iodination. See:
    • In the electrophilic substitution of imidazo[1,5-a]pyridines with acetyl chloride, the course of the reaction is entirely different from usual electrophilic substitution. The imidazole nitrogen atom first attacks the electrophile. Next, the intermediate salt is deprotonated at the C1 (or C3) position. Finally, migration of the electrophile to this position gives the product. Therefore, Lewis acid or base additive may inhibit iodination. See:. Hlasta D.J. Tetrahedron Lett. 31 (1990) 5833
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    • note
    • 3-(4-Nitro-1,1′-biphen-4′-yl)imidazo[1,5-a]pyridine did not show fluorescence emission. See Ref. 5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.