17017-72-0Relevant articles and documents
Pd(OAc)2-catalyzed dehydrogenative C-H activation: An expedient synthesis of uracil-annulated β-carbolinones
Mondal, Biplab,Hazra, Somjit,Panda, Tarun K.,Roy, Brindaban
, p. 1360 - 1366 (2015)
An intramolecular dehydrogenative C-H activation enabled an efficient synthesis of an uracil-annulated β-carbolinone ring system. The reaction is simple, efficient and high yielding (85-92%).
Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction
Arion, Vladimir B.,Bacher, Felix,Chuang, Hsiang-Yu,Kuznetcova, Irina,Vegh, Daniel
, p. 143 - 151 (2022/02/05)
Paullone isomers are known as inhibitors of tubulin polymerase and cyclin dependent kinases (Cdks), which are potential targets for cancer chemotherapy. Herein we report an efficient and clean pathway to the fourth isomer, which remained elusive so far, namely 7,8-dihydroindolo[2,3-d][1]benzazepin-6(5H)-one. Moreover, we demonstrate the generality of our pathway by synthesizing two closely related analogues, one containing a bromo substituent and the other one incorporating an 8-membered instead of a 7-mem-bered ring. The key transformation in this four-step synthesis, with an overall yield of 29%, is the Fischer indole reaction of 2-nitro-phenylacetyl acetoacetate with 1-benzyl-1-phenylhydrazine in acetic acid that delivers methyl 2-(1-benzyl-3-(2-nitrophenyl)-1H-indol-2-yl)acetate in 55% yield.
Synthesis of Indolo[2,3- c]quinolin-6(7 H)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C-H Arylation
Szabó, Tímea,Papp, Marcell,Németh, Dóra Rita,Dancsó, András,Volk, Balázs,Milen, Mátyás
supporting information, p. 128 - 145 (2020/12/22)
The synthesis of variously substituted indolo[2,3-c]quinolin-6(7H)-ones was developed via Pd-catalyzed intramolecular C-H arylation. This method highlights a strategy for preparing indoloquinoline precursors bearing versatile functional groups and provide
Calcium-Catalyzed Formal [5 + 2] Cycloadditions of Alkylidene β-Ketoesters with Olefins: Chemodivergent Synthesis of Highly Functionalized Cyclohepta[ b]indole Derivatives
Parker, Ariel N.,Martin, M. Cynthia,Shenje, Raynold,France, Stefan
supporting information, p. 7268 - 7273 (2019/10/08)
The calcium-catalyzed, formal [5 + 2] cycloaddition of indolyl alkylidene β-ketoesters with mono- A nd disubstituted aryl olefins to form cyclohepta[b]indole derivatives has been established. Unanticipated chemodivergence with phenyl vinyl sulfide/ether revealed a double [5 + 2] cycloaddition cascade providing ethano-bridged cyclohepta[b]indoles. Overall, the method's highlights include: (1) use of a green, calcium-based catalyst (2.5 mol % loading); (2) reaction times under 1 h; (3) mild reaction conditions; (4) substrate-derived chemodivergence; (5) functional group tolerance; and (6) examples of derivatization.
Hydroxamic acids block replication of hepatitis c virus
Ai, Teng,Xu, Yanli,Qiu, Li,Geraghty, Robert J.,Chen, Liqiang
, p. 785 - 800 (2015/01/30)
Intrigued by the role of protein acetylation in hepatitis C virus (HCV) replication, we tested known histone deacetylase (HDAC) inhibitors and a focused library of structurally simple hydroxamic acids for inhibition of a HCV subgenomic replicon. While known HDAC inhibitors with varied inhibitory profiles proved to be either relatively toxic or ineffective, structure-activity relationship (SAR) studies on cinnamic hydroxamic acid and benzo[b]thiophen-2-hydroxamic acid gave rise to compounds 22 and 53, which showed potent and selective anti-HCV activity and therefore are promising starting points for further structural optimization and mechanistic studies.
Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones through a Crystallographically Defined Chiral Dinuclear Nickel Complex
Takeda, Takuya,Harada, Shinji,Nishida, Atsushi
supporting information, p. 5184 - 5187 (2015/11/18)
A Ni(NTf2)2 and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture of the Ni complex and the substrat
BICYCLIC HETEROCYCLIC COMPOUND
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Paragraph 0225, (2014/09/16)
[Problem] To provide a compound useful as an active ingredient of a pharmaceutical composition for treating 11β-hydroxysteroid dehydrogenase type 1-related diseases such as dementia, schizophrenia, depression, pain (particularly, neuropathic pain or fibromyalgia), diabetes (particularly, type II diabetes mellitus), insulin resistance and the like. [Means for Solution] A bicyclic heterocyclic compound (the bicyclic heterocycle is formed when a cyclohexane ring is fused with a 5- to 6-membered monocyclic heterocycle that has only a nitrogen atom as a hetero atom) substituted with an acylamino group such as a (hetero)aroylamino group or the like or a pharmaceutically acceptable salt thereof was found to have an excellent selective inhibitory action against 11β-HSD1. Accordingly, the bicyclic heterocyclic compound of the present invention can be used for treating dementia, schizophrenia, depression, pain (particularly, neuropathic pain or fibromyalgia), diabetes (particularly, type II diabetes mellitus), insulin resistance, and the like.
Heteroaryl cross-coupling as an entry toward the synthesis of lavendamycin analogues: A model study
Verniest, Guido,Wang, Xingpo,De Kimpe, Norbert,Padwa, Albert
experimental part, p. 424 - 433 (2010/03/30)
(Chemical Equation Presented) ABC analogues of the antitumor antibiotic lavendamycin, which contain the key metal chelation site and redox-active quinone unit essential for biological activity, were prepared via the palladium(0)-catalyzed cross-coupling reaction of various 2-haloheteroaromatics with 2-stannylated pyridines and quinolines. Using the Stille reaction, 2-bromo substituted quinolines and 1-bromoisoquinolines were found to undergo efficient coupling with 2-pyridinylstannanes to provide unsymmetrical heterobiaryl derivatives. While the Stille reaction using the reverse coupling partners (i.e., 2-quinolinylstannanes and haloheteroaromatics) had not received much attention in the literature, we found that this alternative coupling reaction efficiently provided several new heterobiaryl derivatives. The gold-catalyzed intramolecular cycloisomerization of N-(prop-2-ynyl)-1H-indole-2-carboxamide smoothly afforded a β-carbolinone derivative that was subsequently used for a Pd(0)-catalyzed cross-coupling directed toward the synthesis of lavendamycin analogues.
Synthesis of substituted β-carbolines via gold(III)-catalyzed cycloisomerization of N-propargylamides
Verniest, Guido,England, Dylan,De Kimpe, Norbert,Padwa, Albert
experimental part, p. 1496 - 1502 (2010/04/02)
Indole-substituted N-propargylamides undergo a gold(III)-catalyzed cyclization to give oxazoles or β-carbolinones, depending on the substitution pattern at the amide nitrogen. Secondary amides furnished oxazoles via a 5-exo-dig cyclization, while tertiary
Synthesis of β- And γ-carbolinones via Pd-catalyzed direct dehydrogenative annulation (DDA) of indole-carboxamides with alkynes using air as the oxidant
Shi, Zhuangzhi,Cui, Yuxin,Jiao, Ning
supporting information; experimental part, p. 2908 - 2911 (2010/09/18)
A palladium-catalyzed direct dehydrogenative annulation (DDA) of indolecarboxamides with internal alkynes via C-H and N-H bond cleavage using air as the oxidant was developed. With this method, both β- and γ-carbolinones can be easily prepared under the mild conditions.
