合成路线:By reaction of 10-(3-chloropropionyl)-2-(ethoxycarbonylamino)phenothiazine (I) with diethylamine in refluxing toluene.
合成路线:This compound can be obtained in two different ways:1) The bromination of 1-(2-ethylindan-2-yl)-1-ethanone (I) with Br2 in ether gives 2-bromo-1-(2-ethylindan-2-yl)-1-ethanone (II),which is then cyclized with formamide by heating at 170-80 C.2) The cyclization of alpha,alpha'-dibromo-o-xylene (III) with 4-penten-2-one (IV) by means of tetrabutylammonium hydroxide in toluene at 100 C gives 1-(2-vinylindan-2-yl)-1-ethanone (V),which is brominated with Br2 in dichloromethane to yield 2-bromo-1-(2-vinylindan-2-yl)-1-ethanone (VI).The cyclization of (VI) with formamide at 160 C as before affords 4-(2-vinylindan-2-yl)-1H-imidazole (VII),which is finally hydrogenated with H2 over Pd/C in ethanol.
参考文献标题:4(5)-Substd.imidazole derivs.,and intermediates and processes for their preparation
文献作者:Karjalainen,A.L.; Karjalainen,A.J.(Orion Pharma)
参考来源:EP 0247764; US 4933359
合成路线:This compound can be obtained in two different ways:1) The bromination of 1-(2-ethylindan-2-yl)-1-ethanone (I) with Br2 in ether gives 2-bromo-1-(2-ethylindan-2-yl)-1-ethanone (II),which is then cyclized with formamide by heating at 170-80 C.2) The cyclization of alpha,alpha'-dibromo-o-xylene (III) with 4-penten-2-one (IV) by means of tetrabutylammonium hydroxide in toluene at 100 C gives 1-(2-vinylindan-2-yl)-1-ethanone (V),which is brominated with Br2 in dichloromethane to yield 2-bromo-1-(2-vinylindan-2-yl)-1-ethanone (VI).The cyclization of (VI) with formamide at 160 C as before affords 4-(2-vinylindan-2-yl)-1H-imidazole (VII),which is finally hydrogenated with H2 over Pd/C in ethanol.
参考文献标题:Atipamezole
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1990,15(5),448
合成路线:A new synthesis of atipamezole has been described:The cyclization of alpha,alpha'-dibromo-o-xylene (I) with acetylacetone (II) by means of NaOH and tetrabutylammonium bromide in toluene/water at 80 C under phase-transfer conditions gives the unstable diacetyl derivative (III),which presumably undergoes cleavage to afford 2-acetylindane (IV).The alkylation of (IV) with ethyl iodide and potassium tert-butoxide yields 2-acetyl-2-ethylindane (V),which is brominated with Br2 to give 2-(bromoacetyl)-2-ethylindane (VI).Finally,this compound is cyclized with formamide at 160 C [some 2-ethyl-2-(4-oxazolyl)indane is also formed but is easily eliminated]; the cyclization can also be carried out with formamidine in liquid ammonia.
参考文献标题:A concise synthesis of atipamezole
文献作者:Wong,W.C.; Gluchowski,C.
参考来源:Synthesis 1995,2(2),139
合成路线:The alkylation of indane-2-carboxylic acid methyl ester (I) with ethyl iodide by means of lithium isopropylcyclohexylamide (LiICA) in THF/DMSO gives the 2-ethyl substituted compound (II),which is hydrolyzed with tBu-OK in DMSO,yielding 2-ethylindane-2-carboxylic acid (III).The reaction of (III) with methanesulfonyl chloride and diazomethane affords the alpha-diazoketone (IV),which is treated with dimethyldioxirane (DMDO) in acetone to provide the ketoaldehyde (V).Finally,this compound is cyclized with 11C-formaldehyde and NH4OH by means of ZnO in THF/water to yield the target labeled imidazole derivative.The intermediate ketoaldehyde (V) has also been obtained in two other ways: a) The alkylation of 2-(diethoxyacetyl)indane (VI) with ethyl iodide by means of tBu-OK in THF gives the corresponding 2-ethyl-substituted compound (VII),which is finally hydrolyzed to the desired ketoaldehyde (V) with HCl in THF/water.b) The oxidation of 2-acetyl-2-ethylindane (VIII) with SeO2 in hot acetic acid/water gives also the desired ketoaldehyde (V).
参考文献标题:Synthesis of [11C]atipamezole,a potential PET ligand for the alpha2-adrenergic receptor in the brain
文献作者:Roeda,D.; et al.
参考来源:J Label Compd Radiopharm 2002,45(1),37
合成路线:This compound can be obtained in two different ways:1) The bromination of 1-(2-ethylindan-2-yl)-1-ethanone (I) with Br2 in ether gives 2-bromo-1-(2-ethylindan-2-yl)-1-ethanone (II),which is then cyclized with formamide by heating at 170-80 C.2) The cyclization of alpha,alpha'-dibromo-o-xylene (III) with 4-penten-2-one (IV) by means of tetrabutylammonium hydroxide in toluene at 100 C gives 1-(2-vinylindan-2-yl)-1-ethanone (V),which is brominated with Br2 in dichloromethane to yield 2-bromo-1-(2-vinylindan-2-yl)-1-ethanone (VI).The cyclization of (VI) with formamide at 160 C as before affords 4-(2-vinylindan-2-yl)-1H-imidazole (VII),which is finally hydrogenated with H2 over Pd/C in ethanol.
参考文献标题:Purified rat hepatic beta2-adrenergic receptor: Structural similarities in the rat fat cell beta1-adrenergic receptor
文献作者:Graziano,M.P.; Maxham,C.P.; Malbon,C.C.
参考来源:J Biol Chem 1985,2607665-74
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