127485-48-7Relevant articles and documents
Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas
Clayden, Jonathan,Fraser, Laura A.,Hill, Jessica E.,Lefebvre, Quentin
, p. 5770 - 5773 (2018)
The base-promoted dearomatizing cyclization of anionic indole-containing urea derivatives provided tri- or tetracyclic indoline-containing scaffolds from lithiated urea intermediates. 3-Substituted indoles, including tryptamine derivatives, generally underwent the reaction in high yield and with excellent diastereoselectivity. In situ IR spectroscopy suggests a deprotonation-carbolithiation-reprotonation mechanism.
A Cascade C–H-Functionalization/Cyclization Reaction of Indoles with α-Halo or α-Sulfonyloxy Ketones for the Synthesis of Dihydropyrimidoindolone Derivatives
Wu, Zi-Jun,Li, Ya-Qiong,Huang, Zhi-Zhen
, p. 5399 - 5404 (2016)
A new cascade C–H-functionalization/cyclization reaction of N-carbamoylindoles 1 with α-halo, α-mesyloxy, or α-tosyloxy ketones 2 has been developed under rhodium(III) catalysis, leading to dihydropyrimido[1,6-a]indolone derivatives 3 in moderate to excellent yields.
Ruthenium(II)-Catalyzed Regio- and Stereoselective C-H Allylation of Indoles with Allyl Alcohols
Wu, Xiaowei,Ji, Haitao
supporting information, p. 2224 - 2227 (2018/04/30)
A ruthenium-catalyzed C-H allylation of indoles with allyl alcohols via β-hydroxide elimination is reported. Without external oxidants and expensive additives, this reaction features mild reaction conditions, compatibility with various functional groups, and good to excellent regioselectivity and stereoselectivity.
Ruthenium(II)-Catalyzed Redox-Neutral [3+2] Annulation of Indoles with Internal Alkynes via C-H Bond Activation: Accessing a Pyrroloindolone Scaffold
Xie, Yanan,Wu, Xiaowei,Li, Chunpu,Wang, Jiang,Li, Jian,Liu, Hong
, p. 5263 - 5273 (2017/05/24)
Ru(II)-catalyzed redox-neutral [3+2] annulation reactions of N-ethoxycarbamoyl indoles and internal alkynes via C-H bond activation are reported. This method features a broad internal alkyne scope, including various aryl/alkyl-, alkyl/alkyl-, and diaryl-substituted alkynes, good to excellent regioselectivity, diverse functional group tolerance, and mild reaction conditions. The N-ethoxycarbamoyl directing group, temperature, CsOAc, and ruthenium catalyst proved to be crucial for conversion and high regioselectivity. Additionally, preliminary mechanistic experiments were conducted, and a possible mechanism was proposed.
THERAPEUTIC COMPOUNDS AND COMPOSITIONS
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Page/Page column 134, (2014/05/07)
Provided are aryl sulfonamide diarylurea derivative compounds that are inhibitors of mutant isocitrate dehydrogenase 1/2 (IDH 1/2), useful for treating cancer. Also provided are methods of treating cancer comprising administering to a subject in need thereof a compound described herein. Cancers that are treatable by the compounds of the invention are glioblastoma, myelodysplastic syndrome, myeloproliferative neoplasm, acute myelogenous leukemia, sarcoma, melanoma, non-small cell lung cancer, chondrosarcoma, and non-Hodgkin's lymphoma (NHL).
Rh(III)-catalyzed selective coupling of N-methoxy-1H-indole-1-carboxamides and aryl boronic acids
Zheng, Jing,Zhang, Yan,Cui, Sunliang
supporting information, p. 3560 - 3563 (2014/07/21)
A Rh(III)-catalyzed selective coupling of N-methoxy-1H-indole-1-carboxamide and aryl boronic acids is reported. The coupling is mild and efficient toward diverse product formation, with selective C-C and C-C/C-N bond formation. Kinetic isotope effects studies were conducted to reveal a mechanism of C-H activation and electrophilic addition.
Direct allylation of aromatic and α,β-unsaturated carboxamides under ruthenium catalysis
Kim, Mirim,Sharma, Satyasheel,Mishra, Neeraj Kumar,Han, Sangil,Park, Jihye,Kim, Minyoung,Shin, Youngmi,Kwak, Jong Hwan,Han, Sang Hoon,Kim, In Su
supporting information, p. 11303 - 11306 (2014/11/07)
The ruthenium-catalyzed oxidative allylation of aromatic and α,β-unsaturated carboxamides with allylic carbonates is described. These transformations proceed readily with complete linear γ-selectivity of substituted allylic carbonates. the Partner Organisations 2014.
Synthesis of unsymmetrical 2,20-Biindolyl derivatives by a Cu-Catalyzed N-Arylation/ Pd-catalyzed direct arylation sequential process
Wang, Zhi-Jing,Yang, Fan,Lv, Xin,Bao, Weiliang
supporting information; experimental part, p. 967 - 970 (2011/04/16)
A one-pot synthesis of unsymmetrical 2,20-biindolyl derivatives through a Cu-catalyzed N-arylation/Pd-catalyzed direct arylation sequence was described. The reaction involved easily prepared o-gem-dibromovinyl substrates, and the desired biindolyls were obtained in moderate to good yields.
Hydrolysis of Ureas. Kinetics and Mechanism of the Basic Hydrolysis of Indole-1-carboxamides and (5H-Dibenzoazepine)-5-carboxamide
Linda, Paolo,Ebert, Cynthia,Lovrecich, Mara,Rubessa, Fulvio
, p. 271 - 272 (2007/10/02)
The hydroxide ion catalyzed hydrolysis of indole-1-carboxamide and indole-1-(N,N-dimethyl)carboxamide has been studied in water at 60.0 deg C and -> concentration between 0.3-2.4 N.The rate constants of formation of the tetrahedral intermediate are strongly increased by N-substitution with a heteroaromatic ring in comparison with simple amides.Carbamazepine, (5H-dibenzazepine)-5-carboxamide, a potent anticonvulsant drug, is particularly stable under these conditions.
