IMIDAZOLE DERIVATIVES .3. REGIOSPECIFIC SYNTHESIS, STRUCTURE, AND FLUORESCENCE PROPERTIES OF HIGHLY SUBSTITUTED IMIDAZO[1,2-A]PYRIDINES AND PYRIDO[1,2-A]BENZIMIDAZOLES

被引：57

作者：

KNOLKER, HJ ^{[1
]}

BOESE, R ^{[1
]}

HITZEMANN, R ^{[1
]}

机构：

[1] UNIV GESAMTHSCH ESSEN,INST ANORGAN CHEM,W-4300 ESSEN 1,GERMANY

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 02期

关键词：

Dimethyl acetylenedicarboxylate / Imidazo[1,2‐a]pyridines / Pyrido[1,2‐a]benzimidazoles / Fluorescence, imidazo[1,2‐a]pyridines;

D O I：

10.1002/cber.19901230218

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1‐(Arylacetyl)imidazoles 1 react with acetylenedicarboxylic esters to provide highly functionalized imidazo[1,2‐a]pyridines 2 in up to 89% yield. The scope and limitations of this novel condensation reaction have been investigated, ad a mechanistic interpretation is presented. A strong effect on the yield of this reaction is observed for electron‐donating and electronwithdrawing substituents in the para position of the aryl ring. Moreover, the transformation is shown to proceed in a regiospecific manner starting with 4,5‐unsymmetrically substituted 1‐(arylacetyl)imidazoles (1d–g) and is extended to the synthesis of the corresponding pyrido[1,2‐a]benzimidazoles 12. The crystal structure of derivative 2a has been determined by X‐ray analysis. Imidazo[1,2‐a]pyridines 2 and pyrido[1,2‐a]‐benzimidazoles 12, obtained by this procedure, are highly fluorescent in the visible region with characteristically large Stokes shifts. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

引用

页码：327 / 339

页数：13

共 79 条

[1] REACTIONS OF ACETYLENECARBOXYLIC ACIDS AND THEIR ESTERS WITH NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS [J].

ACHESON, RM .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1963, 1 :125-165

[2]

ACHESON RM, 1978, ADV HETEROCYCL CHEM, V23, P263

[3]

ACHESONRM, 1967, J CHEM SOC C, P882

[4]

ADELSTEIN GW, 1988, Patent No. 4721718

[5]

[Anonymous], 1984, COMPR HETEROCYCL CHE, DOI [10.1016/B978-008096519-2.00080-1, DOI 10.1016/B978-008096519-2.00080-1]

[6] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[7] SPECIES RESPONSIBLE FOR FLUORESCENCE OF 3,N4-ETHENOCYTIDINE [J].

BARRIO, JR ;

SATTSANGI, PD ;

GRUBER, BA ;

DAMMANN, LG ;

LEONARD, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (23) :7408-7414

[8]

BASTIAANSEN LAM, 1978, SYNTHESIS-STUTTGART, P675

[9] MECHANISM OF GASTRIC ANTISECRETORY EFFECT OF SCH-28080 [J].

BEIL, W ;

HACKBARTH, I ;

SEWING, KF .

BRITISH JOURNAL OF PHARMACOLOGY, 1986, 88 (01) :19-23

[10]

BEYERMAN HC, 1972, RECL TRAV CHIM PAY-B, V91, P246

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