Easy access to novel substituted 6-aminoimidazo[1,2-a]pyridines using palladium- and copper-catalyzed aminations

被引：77

作者：

Enguehard, C

Allouchi, H

Gueiffier, A

Buchwald, SL

机构：

[1] UFR Sci Pharmaceut, Chim Therapeut Lab, EA 3247, F-37200 Tours, France

[2] UFR Sci Pharmaceut, Chim Phys Lab, F-37200 Tours, France

[3] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 11期

关键词：

D O I：

10.1021/jo0341463

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Convenient and efficient methods for the preparation of novel 6-aminoimidazo[1,2-a]pyridine derivatives are reported that utilized palladium- or copper-catalyzed methodology. The crystal structure for 6-N-methylanilinoimidazo[1,2-a]pyridine 10 is also described.

引用

页码：4367 / 4370

页数：4

共 44 条

[1] Mechanistic studies on oxidative addition of aryl halides and triflates to Pd(BINAP)2 and structural characterization of the product from aryl triflate addition in the presence of amine
Alcazar-Roman, LM
Hartwig, JF
[J]. ORGANOMETALLICS, 2002, 21 (03) : 491 - 502
[2] Mechanism of aryl chloride amination: Base-induced oxidative addition
Alcazar-Roman, LM
Hartwig, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) : 12905 - 12906
[3] Imidazo[4,5-b]pyridines as corticotropin releasing factor receptor ligands
Arvanitis, AG
Rescinito, JT
Arnold, CR
Wilde, RG
Cain, GA
Sun, JH
Yan, JS
Teleha, CA
Fitzgerald, LW
McElroy, J
Zaczek, R
Hartig, PR
Grossman, S
Arneric, SP
Gilligan, PJ
Olson, RE
Robertson, DW
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (01) : 125 - 128
[4] Palladium-catalyzed amination of 6-chloropurine.: Synthesis of N6-substituted adenosine analogues
Barends, J
van der Linden, JB
van Delft, FL
Koomen, GJ
[J]. NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (09): : 2121 - 2126
[5] Ortho-directed metalation of 3-carboxy-β-carbolines:: Use of the SmI2-cleavable 9-N-(N′,N′-dimethylsulfamoyl) blocking group for the preparation of 9-N-deprotected 4-amino derivatives via azide introduction or a palladium-catalyzed cross-coupling reaction
Batch, A
Dodd, RH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) : 872 - 877
[6] BLACHE Y, 1994, HETEROCYCLES, V38, P1527
[7] Synthesis of biologically active N2-amine adducts of 2′-deoxyguanosine
Bonala, RR
Shishkina, IG
Johnson, F
[J]. TETRAHEDRON LETTERS, 2000, 41 (38) : 7281 - 7284
[8] BRISTOL JA, 1982, Patent No. 450885
[9] Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines:: Synthesis of 6-(β-D-mannopyranosylamino)-9H-purine and its β-D-gluco isomer, N-glycoside models for spicamycin and septacidin
Chida, N
Suzuki, T
Tanaka, S
Yamada, I
[J]. TETRAHEDRON LETTERS, 1999, 40 (13) : 2573 - 2576
[10] Hybrid-designed inhibitors of p38 MAP kinase utilizing N-arylpyridazinones
Colletti, SL
Frie, JL
Dixon, EC
Singh, SB
Choi, BK
Scapin, G
Fitzgerald, CE
Kumar, S
Nichols, EA
O'Keefe, SJ
O'Neill, EA
Porter, G
Samuel, K
Schmatz, DM
Schwartz, CD
Shoop, WL
Thompson, CM
Thompson, JE
Wang, RX
Woods, A
Zaller, DM
Doherty, JB
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (03) : 349 - 352

← 1 2 3 4 5 →