119668-50-7Relevant academic research and scientific papers
Re-Catalyzed Annulations of Weakly Coordinating N-Carbamoyl Indoles/Indolines with Alkynes via C?H/C?N Bond Cleavage
Yang, Yunhui,Wang, Congyang
supporting information, p. 8245 - 8248 (2019/05/28)
Described herein are rhenium-catalyzed [3+2] annulations of N-carbamoyl indoles with alkynes via C?H/C?N bond cleavage, which provide rapid access to fused-ring pyrroloindolone derivatives. For the first time, the weakly coordinating O-directing group was successfully employed in rhenium-catalyzed C?H activation reactions, enabled by the unique catalytic trio of Re2(CO)10, Me2Zn and ZnCl2. Mechanistic studies revealed that aminozinc species plays an important role in the reaction. Based on the mechanistic understanding, a more powerful catalytic trio of Re2(CO)10, [MeZnNPh2]2 and Zn(OTf)2 was devised and applied successfully in the [4+2] annulations of indolines and alkynes affording pyrroloquinolinone derivatives.
Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage
Ye, Lu,Cai, Sai-Hu,Wang, Ding-Xing,Wang, Yi-Qiu,Lai, Lin-Jie,Feng, Chao,Loh, Teck-Peng
supporting information, p. 6164 - 6167 (2017/11/24)
A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.
C-H activation by amide chelation control: Ruthenium-catalyzed direct synthesis of 2-Aryl-3-furanamides
Zhao, Yigang,Snieckus, Victor
supporting information, p. 1527 - 1532 (2014/06/09)
A new, catalytic methodology for the synthesis of heterobiaryls by the ruthenium-catalyzed C-H activation/cross-coupling of heterocyclic amides with aryl boroneopentylates is surveyed. From this survey, the highly regioselective reaction of furan-3-carboxamide to give 2-aryl-3-furanamides is optimized and generalized in scope with respect to the aryl boroneopentylate coupling partners. Established thereby is a one-step synthetic method which may supercede the broadly applied two-step directed ortho metalation (DoM)-cross coupling reaction involving cryogenic and strong base conditions and which has potential for further ortho and remote metalation chemistry.
Automated generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors
Tricotet, Thomas,O'Shea, Donal F.
experimental part, p. 6678 - 6686 (2010/08/20)
An automated sequential approach for the generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors is described. Consecutive halogen-magnesium exchanges of four 3-iodoindoles followed by addition to three aldehydes provided twelv
Schwartz Reagents: Methods of In Situ Generation and Use
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Page/Page column 8, (2010/06/19)
Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.
Directed ortho metalation approach to C-7-substituted indoles. Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone alkaloids
Hartung, Christian G.,Fecher, Anja,Chapell, Brian,Snieckus, Victor
, p. 1899 - 1902 (2007/10/03)
(Matrix presented) Although the indole N-phosphinoyl derivative 4 undergoes n-BuLi deprotonation/electrophile quench to afford C-7-substituted products, its deprotection requires harsh conditions. On the other hand, the N-amide 12, upon sequential or one-pot C-2 metalation, silylation, C-7 metalation, and electrophile treatment, furnishes indoles 7 in good overall yields. In combination with the Suzuki-Miyaura protocol, C-7 aryl (heteroaryl)-substituted indoles 14 and 16 are obtained, including hippadine and pratosine, members of the pyrrolophenanthridone alkaloid family.
Synthesis and reactivity of 2-(1,3-dithian-2-yl)indoles. IV. Influence of the N,N-deithylcarbamoyl indole protecting group
Castells,Troin,Diez,Rubiralta,Grierson,Husson
, p. 7911 - 7924 (2007/10/02)
The effect of the N,N-diethylcarbamoyl indole protecting group on the reactivity of 2-(1,3-dithian-2-yl)indole 7 in front of a series of electrophiles, as well as the potential synthetic usefulness of the resulting 2,2-disubstituted dithianes is reported.
THE MANGANESE(III) ACETATE OXIDATION OF N-PROTECTED INDOLINES
Ketcha, Daniel M.
, p. 2151 - 2154 (2007/10/02)
A variety of N-protected indolines can be oxidized to the corresponding indoles using manganese(III) acetate in glacial acetic acid.
