Synthesis of trisubstituted imidazoles by palladium-catalyzed cyclization of O-pentafluorobenzoylamidoximes:: Application to amino acid mimetics with a C-terminal imidazole

被引：122

作者：

Zaman, S

Mitsuru, K

Abell, AD

机构：

[1] Univ Canterbury, Dept Chem, Christchurch, New Zealand

[2] Univ Tokyo, Grad Sch Sci, Bunkyo Ku, Tokyo, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 04期

关键词：

D O I：

10.1021/ol047628p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Benzyl-4-methylimidazoles with a range of substituents at the 2-position are prepared from O-pentafluorobenzoylamidoximes on treatment with catalytic amounts of Pd(PPh3)(4) and triethylamine. The sequence provides access to optically active amino acid mimetics with a C-terminal imidazole.

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收藏

页码：609 / 611

页数：3

相关论文

共 25 条

[11] MECHANISMS AND STEREOCHEMISTRY OF AMINE SUBSTITUTION-REACTIONS AT THE CARBON NITROGEN DOUBLE-BOND [J].

JOHNSON, JE ;

TODD, SL ;

DUTSON, SM ;

GHAFOURIPOUR, A ;

ALDERMAN, RM ;

HOTEMA, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) :4648-4653

[12] Synthesis of aza-heterocycles from oximes by amino-Heck reaction [J].

Kitamura, M ;

Narasaka, K .

CHEMICAL RECORD, 2002, 2 (04) :268-277

[13] Palladium-catalyzed synthesis of 1-azaazulenes from cycloheptatrienylmethyl ketone O-pentafluorobenzoyl oximes [J].

Kitamura, M ;

Chiba, S ;

Saku, O ;

Narasaka, K .

CHEMISTRY LETTERS, 2002, (06) :606-607

[14] Discovery of 3-amino-4-chlorophenyl P1 as a novel and potent benzamidine mimic via solid-phase synthesis of an isoxazoline library [J].

Lam, PYS ;

Adams, JJ ;

Clark, CG ;

Calhoun, WJ ;

Luettgen, JM ;

Knabb, RM ;

Wexler, RR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (10) :1795-1799

[15] Imidazolylidene carbene ligated palladium catalysis of the Heck reaction in the presence of air [J].

Liu, JP ;

Zhao, YH ;

Zhou, YY ;

Li, L ;

Zhang, TY ;

Zhang, HB .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (18) :3227-3231

[16] Triazine-based polyfluorinated triquaternary liquid salts: Synthesis, characterization, and application as solvents in rhodium(I)-catalyzed hydroformylation of 1-octene [J].

Omotowa, BA ;

Shreeve, JM .

ORGANOMETALLICS, 2004, 23 (04) :783-791

[17]

PINKERTON FH, 1972, J HETEROCYCLIC CHEM, V9, P67, DOI 10.1002/jhet.5570090110

[18] A stereospecific synthesis of both enantiomers of 2-(1'-amino-2'-methylpropyl) imidazole, a key synthon in the synthesis of SB 203386; A potent protease inhibitor [J].

Pridgen, LN ;

Mokhallalati, MK ;

McGuire, MA .

TETRAHEDRON LETTERS, 1997, 38 (08) :1275-1278

[19] BACKBONE-MODIFIED OLIGOPEPTIDIC BIOREGULATORS - THE SYNTHESIS AND CONFIGURATION OF THIOAMIDE, AMIDOXIME, CYANOAMIDINE, AND AMIDRAZONE ANALOGS OF THE CHEMOTACTIC PEPTIDE N-FORMYL-METHIONYL-LEUCYL-PHENYLALANINE (F-MET-LEU-PHE-OR) [J].

SAUVE, G ;

RAO, VS ;

LAJOIE, G ;

BELLEAU, B .

CANADIAN JOURNAL OF CHEMISTRY, 1985, 63 (11) :3089-3101

[20] Synthesis of pyrrole derivatives by palladium-catalyzed cyclization of γδ-unsaturated ketone O-pentafluorobenzoyloximes [J].

Tsutsui, H ;

Kitamura, M ;

Narasaka, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2002, 75 (07) :1451-1460