- Nucleophilic Iron Complexes in Proton-Transfer Catalysis: An Iron-Catalyzed Dimroth Cyclocondensation
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The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) is an active catalyst in C?H-amination but also in proton-transfer catalysis. Herein, we describe the successful use of this complex as a proton-transfer catalyst in the cyclocondensation reaction between azides and ketones to the corresponding 1,2,3-triazoles. Cross-experiments indicate that the proton-transfer catalysis is significantly faster than the nitrene-transfer catalysis, which would lead to the C?H amination product. An example of a successful sequential Dimroth triazole–indoline synthesis to the corresponding triazole-substituted indolines is presented.
- Baykal, Aslihan,Zhang, Dihan,Knelles, Jakob,Alt, Isabel T.,Plietker, Bernd
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supporting information
p. 3003 - 3010
(2019/08/21)
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- Regioselective Synthesis of Indolopyrazines through a Sequential Rhodium-Catalyzed Formal [3+3] Cycloaddition and Aromatization Reaction of Diazoindolinimines with Azirines
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A regioselective synthetic method for the preparation of indolopyrazines was demonstrated through a sequential Rh-catalyzed formal [3+3] cycloaddition and aromatization reaction of a wide range of diazoindolinimines with azirines. Because the previously reported synthetic methods afforded mixtures of indolopyrazines, the present method using unsymmetrical azirines has a strong advantage from a regioselectivity viewpoint.
- Baek, Yonghyeon,Maeng, Chanyoung,Kim, Hyunseok,Lee, Phil Ho
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p. 2349 - 2360
(2018/02/23)
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- Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide
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A facile synthesis of polysubstituted pyrroles from tosylmethyl isocyanide (TOSMIC) and readily synthesized vinyl azides was developed. The reaction proceeded under mild conditions in the presence of base. 2-Tosyl-substituted pyrroles were obtained in moderate to good isolated yields. Additionally, a base-initiated one-pot pyrrole synthesis also was developed using carboxaldehydes, ethyl 2-azidoacetate, and TOSMIC.
- Chen, Wenteng,Shao, Jiaan,Li, Zhi,Giulianotti, Marc A.,Yu, Yongping
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p. 214 - 221
(2012/03/07)
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- Simple and facile method for the preparation of vinyl azides
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A synthetic utility of [bis(trifluoroacetoxy)iodo]benzene on α,β-unsaturated carboxylic acid is described. This is the first example of preparation of vinyl azide using α,β-unsaturated carboxylic acids directly by using hypervalent iodine reagent. The adv
- Telvekar, Vikas N.,Takale, Balaram S.,Bachhav, Harshal M.
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scheme or table
p. 5056 - 5058
(2009/12/05)
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- Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds
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(Chemical Equation Presented) Two synthetic methods for tetra- and trisubstituted N-H pyrroles are presented: (i) the thermal pyrrole formation by the reaction of vinyl azides with 1,3-dicarbonyl compounds via the 1,2-addition of 1,3-dicarbonyl compounds to 2H-azirine intermediates generated in situ from vinyl azides; (ii) the Cu(II)-catalyzed synthesis of pyrroles from α-ethoxycarbonyl vinyl azides and ethyl acetoacetate through the 1,4-addition reaction of the acetoacetate to the vinyl azides. By applying these two methods, regioisomeric pyrroles can be prepared selectively starting from the same vinyl azides.
- Chiba, Shunsuke,Wang, Yi-Feng,Lapointe, Guillaume,Narasaka, Koichi
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p. 313 - 316
(2008/09/19)
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- A novel synthesis of α-azidocinnamates, α-azido-α,β-unsaturated ketones and β-azidostyrenes mediated by cerium(IV) ammonium nitrate
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Cerium(IV) ammonium nitrate mediated addition of azide to cinnamic esters, acids and α,β-unsaturated ketones, followed by reaction with sodium acetate afforded the α-azidocinnamates, β-azidostyrenes and α-azido-α,β- unsaturated ketones, respectively, in good yields. (C) 2000 Elsevier Science Ltd.
- Nair, Vijay,George, Tesmol G.
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p. 3199 - 3201
(2007/10/03)
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