A SIMPLE AND PRACTICAL SYNTHESIS OF 2-AMINOIMIDAZOLES

被引：127

作者：

LITTLE, TL ^{[1
]}

WEBBER, SE ^{[1
]}

机构：

[1] AGOURON PHARMACEUT INC, SAN DIEGO, CA 92121 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 24期

关键词：

D O I：

10.1021/jo00103a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

引用

收藏

页码：7299 / 7305

页数：7

相关论文

共 59 条

[1] HYPOXIA-MEDIATED NITRO-HETEROCYCLIC DRUGS IN THE RADIOTHERAPY AND CHEMOTHERAPY OF CANCER - AN OVERVIEW [J].

ADAMS, GE ;

STRATFORD, IJ .

BIOCHEMICAL PHARMACOLOGY, 1986, 35 (01) :71-76

[2] NOVEL MARINE SPONGE ALKALOIDS .2. STRUCTURES AND TOTAL SYNTHESIS OF 2-AMINOIMIDAZOLES FROM A NOTODORIS NUDIBRANCH [J].

ALVI, KA ;

CREWS, P ;

LOUGHHEAD, DG .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (06) :1509-1515

[3] 2-AMINOIMIDAZOLES AND THEIR ZINC-COMPLEXES FROM INDO-PACIFIC LEUCETTA SPONGES AND NOTODORIS NUDIBRANCHS [J].

ALVI, KA ;

PETERS, BM ;

HUNTER, LM ;

CREWS, P .

TETRAHEDRON, 1993, 49 (02) :329-336

[4]

[Anonymous], 1993, ANN DRUG DATA REP, V15, P513

[5] PYRROLE ANTIBACTERIAL AGENTS .2. 4,5-DIHALOPYRROLE-2-CARBOXYLIC ACID DERIVATIVES [J].

BAILEY, DM ;

JOHNSON, RE .

JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (11) :1300-1302

[6] SYNTHESIS OF AZOMYCIN [J].

BEAMAN, AG ;

TAUTZ, W ;

GABRIEL, T ;

DUSCHINSKY, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (02) :389-+

[7]

BEDOYAZURITA M, 1989, TETRAHEDRON, V45, P6713

[8] SYNTHESIS OF 8-AMINO-3-DEAZAGUANINE VIA IMIDAZOLE PRECURSORS - ANTITUMOR-ACTIVITY AND INHIBITION OF PURINE NUCLEOSIDE PHOSPHORYLASE [J].

BERRY, DA ;

GILBERTSEN, RB ;

COOK, PD .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (10) :2034-2037

[9] REACTIONS OF ALPHA-HALOKETO COMPOUNDS WITH GUANIDINE COMPOUNDS .1. SYNTHESIS OF NEW IMIDAZOLE DERIVATIVES [J].

BEYER, H ;

HETZHEIM, A ;

HONECK, H ;

LING, DL ;

PYL, T .

CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (09) :3151-&

[10] SYNTHESIS OF PARAZOANTHOXANTHINS AND PSEUDOZOANTHOXANTHINS [J].

BRAUN, M ;

BUCHI, G ;

BUSHEY, DF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (13) :4208-4213

← 1 2 3 4 5 6 →