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2. Palladium-Catalyzed Intramolecular Cyclization Reaction Abell and co-workers recently developed a new synthetic method for trisubstituted imidazoles, 2-substituted 1-benzyl-4- methylimidazoles 2, based on the palladium-catalyzed intramolecular amino-Heck reaction of amidoximes 1 (Scheme 1).[15] With the success of the catalytic imidazole synthesis by the Pd-catalyzed intramolecular cyclization reaction, which employed relatively simple amidoximes, Abell and co-workers applied this transformation to the substrates prepared from amino acids to introduce an imidazole moiety as a stable ester isostere at the C terminus of peptidomimetics[23] (Scheme 2). 3. Palladium-Catalyzed Multicomponent Coupling Reaction Siamaki and Arndtsen succeeded in developing a direct synthesis of imidazoles by the palladium-catalyzed multicomponent coupling reaction (MCR) starting from two imines 3 and 5 and acid chlo- ACHTUNGTRENUNGrides 4 under CO atmosphere (Scheme 4).[16] In the early stages of the investigation, Siamaki and Arndtsen suffered low yields of the desired imidazole due to the formation of undesired a-sulfonylamide 7 and amide 8 (Scheme 5). 4. d10（10为上标）-Metal-Catalyzed Cycloaddition Reaction As shown in Scheme 7, only two examples were reported. The reaction of isocyanides 9a and 9b afforded the corresponding imidazoles 10 a and 10b in excellent yields. During the course of our research on the copper-catalyzed synthesis of pyrroles starting from isocyanides and acetylenes conjugated with an electron- withdrawing group (EWG),[31] we encountered homodimerization of ethyl isocyanoacetate (12 a, EWG=CO2Et; Scheme 9) with a catalytic amount of Cu2O and 1,10-phen- ACHTUNGTRENUNGanthroline (phen) to produce 1-(ethoxycarbonylmethyl)-4- (ethoxycarbonyl)imidazole (10 c, R=Et; Scheme 7) in 49% yield. 5. Lewis AcidCatalyzedMulticomp onent Coupling Reaction In this context, Sharma et al. investigated a Lewis acid catalyzed synthesis of imidazoles. They surveyed the three-component coupling reaction (TCR) of benzil, aldehydes 14, and NH4OAc in the presence of a catalytic amount of ZrCl4 and observed a dramatic acceleration in imidazole formation (Scheme 11).[19] The ZrCl4-catalyzed four-component coupling reaction (FCR) was further examined with benzil, benzaldehyde, primary amine 16, and NH4OAc to synthesize the fully substituted imidazoles 17 (Scheme 12). 6. Thiazolium-CatalyzedThree-Com ponent Coupling Reaction Frantz et al. developed the one-pot synthesis of imidazoles through the synthesis of a-ketoamides (N) via the thiazolium- catalyzed addition of aldehydes 19 to acylimines generated from a-sulfonylamides 18[39] and subsequent treatment with amines 20 (Scheme 13).[20] |
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肚而家
木虫 (小有名气)
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RXMCDM: 金币+1, 多谢应助！ 2014-03-12 02:06:00
真强必胜: 金币+5, 谢谢 2014-03-12 10:34:58
zzwanghaitao: 金币+200, 翻译EPI+1, ★★★很有帮助 2014-03-12 12:21:36
RXMCDM: 金币+1, 多谢应助！ 2014-03-12 02:06:00
真强必胜: 金币+5, 谢谢 2014-03-12 10:34:58
zzwanghaitao: 金币+200, 翻译EPI+1, ★★★很有帮助 2014-03-12 12:21:36
肚而家
木虫 (小有名气)
- 翻译EPI: 21
- 应助: 44 (小学生)
- 金币: 1927.2
- 散金: 500
- 红花: 10
- 帖子: 289
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- 虫号: 2926551
- 注册: 2014-01-11
- 性别: GG
- 专业: 有机化学