cas 52598-02-4, 5-Chloro-2,3-diphenyl-1H-indole

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Synthesis of Unprotected and Highly Substituted Indoles by the Ruthenium(II)-Catalyzed Reaction of Phenyl Isocyanates with Diaryl/Diheteroaryl Alkynes/Ethyl-3-phenyl Propiolates
A one-pot transformation has been developed for the synthesis of unprotected and highly substituted indoles by an in situ installed carbamide-directed Ru(II)-catalyzed intermolecular oxidative annulation of phenyl isocyanates with diaryl/diheteroaryl alkynes/ethyl phenyl propiolates in the presence of Cu(OAc)2·H2O as an oxidant and AgSbF6 as an additive at 120 °C within 3 h.
Kumar, Amrendra,Tadigoppula, Narender
supporting information
p. 8 - 12
(2021/01/13)

Step and redox efficient nitroarene to indole synthesis
Step and redox efficiencies are a rising priority in synthetic method development, in order to make synthetic processes more sustainable and more affordable. Herein, a step and redox efficient nitroarene to indole synthesis is developed, in sharp contrast to the rich literature on the construction of indoles. Elemental zinc was found to be the best terminal reductant. This journal is
?zkaya, Bünyamin,Bub, Christina L.,Patureau, Frederic W.
supporting information
p. 13185 - 13188
(2020/11/09)

Method for preparing indole compounds by using rhodium/carbon as catalyst
The invention provides a method for preparing indole compounds by using rhodium/carbon as a catalyst. Corresponding indole compounds are formed through subjecting aniline and analogs thereof and alkyne to a catalytic cyclization reaction in the presence of the rhodium/carbon. The method has the beneficial effects that the preparation method is simple in process, the raw materials are cheap and readily available, the yield is high, inert-gas protection is not required, and the reaction temperature is relatively moderate.
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Paragraph 0029-0031; 0034; 0036

(2018/04/26)

A palladium/carbon as catalyst preparation of indole compounds method (by machine translation)
The present invention provides a palladium/carbon as catalyst preparation of indole compounds method, aniline and its analogs in the palladium/carbon with the alkyne under the action of the catalytic cyclization reaction, to form the corresponding indoles. This method has the advantages of: simple preparation method, the raw material is cheap, high yield, without protection of inert gas, the reaction temperature is relatively mild. (by machine translation)
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Paragraph 0029; 0030; 0031; 0033

(2018/06/15)

Transition-metal-free, visible-light-mediated cyclization of: O -azidoarylalkynes with aryl diazonium salts
Visible light along with 3 mol% eosin Y catalyzes the cyclization reaction of o-azidoarylalkynes with aryl diazonium salts by a photoredox process. We have investigated the scope of the reaction for several aryl diazonium salts and o-azidoarylalkynes. The general and easy procedure provides a transition-metal-free alternative for the formation of unsymmetrical 2,3-diaryl-substitued indoles.
Jin, Cheng,Su, Lianzheng,Ma, Daxi,Cheng, Mingrong
supporting information
p. 14053 - 14056
(2017/11/28)

Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with o-azidoarylalkynes: a regiospecific route to unsymmetrical 2,3-disubstituted indoles
A visible-light-catalyzed synthesis of unsymmetrical 2,3-diaryl-substituted indoles from arylsulfonyl chlorides and o-azidoarylalkynes at room temperature has been discovered. This transformation exhibits excellent substrate scope and functional group tolerance. The use of inexpensive eosin Y as the catalyst with easy operation makes this protocol very practical.
Gu, Lijun,Jin, Cheng,Wang, Wei,He, Yonghui,Yang, Guangyu,Li, Ganpeng
supporting information
p. 4203 - 4206
(2017/04/21)

Selective Synthesis of Indoles by Cobalt(III)-Catalyzed C-H/N-O Functionalization with Nitrones
The redox-neutral annulation of alkynes by differently decorated nitrones set the stage for a step-economical access to indoles with ample substrate scope. The redox-neutral C-H/N-O functionalization process proceeded through kinetically relevant C-H activation by carboxylate assistance, and displayed an excellent site- and regio-selectivity with unsymmetrical nitrones and alkynes.
Wang, Hui,Moselage, Marc,González, María J.,Ackermann, Lutz
p. 2705 - 2709
(2016/04/26)

Cobalt(III)-Catalyzed Redox-Neutral Synthesis of Unprotected Indoles Featuring an N-N Bond Cleavage
A redox-neutral cobalt(III)-catalyzed synthetic approach for the direct synthesis of unprotected indoles showcasing an N-N bond cleavage is reported. The herein newly introduced Boc-protected hydrazines establish a beneficial addition to the limited portfolio of oxidizing directing groups for cobalt(III) catalysis. Moreover, the developed catalytic methodology tolerates a good variety of functional groups.
Lerchen, Andreas,Vásquez-Céspedes, Suhelen,Glorius, Frank
supporting information
p. 3208 - 3211
(2016/03/12)

A kind of high-efficient synthetic indole and isoquinoline derivatives (by machine translation)
The invention discloses a substituted indole and isoquinoline preparation method, which belongs to the technical field of organic chemical synthesis. This method adopts the oxygen as the oxidizing agent, various substituents substituted alkyne starting material of the aromatic amine or [...] , by transition metal-catalyzed, get containing indole or isoquinoline compound of the structure. The reaction raw material, oxidizing agent and cheap and easily obtained catalyst, synthesis technique is simple, which greatly reduces the cost of synthesizing; mild reaction conditions, high yield, easy industrialization; reaction raw materials and catalyst cleaning non-toxic, small pollution to the environment. Such compounds and their derivatives as an important fine chemicals, in the medical, agricultural chemicals, perfume and widely used photoelectric and other industries. (by machine translation)
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Paragraph 0039; 0040

(2016/10/07)

Rhodium(III)-Catalyzed Redox-Neutral C-H Annulation of Arylnitrones and Alkynes for the Synthesis of Indole Derivatives
By using a nitrone as the oxidizing directing group, a mild, practical and efficient rhodium(III)-catalyzed C-H functionalization for the synthesis of indole derivatives has been developed. This reaction obviates the need for an external oxidant and shows good functional group tolerance. The employment of a sterically hindered Mes group on the carbon center of the nitrone is crucial to produce indoles in high yield.
Zhou, Zhi,Liu, Guixia,Chen, Yan,Lu, Xiyan
supporting information
p. 2944 - 2950
(2015/09/28)

INDOLE DERIVATIVE OR SALT THEREOF
PROBLEM TO BE SOLVED: To provide a compound that has excellent aP2 inhibitory action and is useful as medicaments, aP2 inhibitors, and therapeutics for the diseases improved by the inhibition of aP2. SOLUTION: The problem is solved by a compound represented by the general formula (I) (for symbols in the formula, refer to definitions in the specifications) or salt thereof. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0054

(2020/04/17)

Rhodium(iii)-catalysed aerobic synthesis of highly functionalized indoles from N-arylurea under mild conditions through C-H activation
A Rh(iii) catalysed amino arylation of alkynes using copper as the terminal oxidant for regeneration of the catalytically active species under aerobic conditions is described. This novel C-H activation reaction was applied to the synthesis of a wide range of substituted indoles from N-arylureas.
Kathiravan, Subban,Nicholls, Ian A.
supporting information
p. 14964 - 14967
(2014/12/11)

Rh-Catalyzed oxidative C-H activation/annulation: Converting anilines to indoles using molecular oxygen as the sole oxidant
A practical and efficient Rh(iii)-catalyzed aerobic C-H activation has been developed for the facile synthesis of a broad range of indoles from simple anilines and alkynes. The protocol could be conducted under mild conditions and used environmentally friendly oxygen as the sole clear oxidant.
Zhang, Guoying,Yu, Hui,Qin, Guiping,Huang, Hanmin
supporting information
p. 4331 - 4334
(2014/04/17)

Regioselective synthesis of indoles via rhodium-catalyzed C-H activation directed by an in-situ generated redox-neutral group
A regioselective synthesis of indoles from arylhydrazine hydrochlorides with alkynes and diethyl ketone catalyzed by a rhodium complex is described. A possible mechanism involving an in-situ generated oxidizing directing group -N-Ni'CR1R2 assisted ortho-C-H activation and reductive elimination are proposed. The catalytic reaction is highly compatible with a wide range of functional arylhydrazines and alkynes. The reaction proceeds under mild reaction conditions and is atom-step economical.
Muralirajan, Krishnamoorthy,Cheng, Chien-Hong
supporting information
p. 1571 - 1576
(2014/06/09)

Rhodium(III)-catalyzed c-h activation and indole synthesis with hydrazone as an auto-formed and auto-cleavable directing group
An efficient, practical, and external-oxidant-free indole synthesis from readily available aryl hydrazines was developed, by using hydrazone as a directing group for RhIII-catalyzed C-H activation and alkyne annulation. The hydrazone group was formed by in situ condensation of hydrazines and Ci￡O source, whereas its N-N bond was served as an internal oxidant, for which we termed it as an auto-formed and auto-cleavable directing group (DGauto). This method needs no step for pre-installation and post-cleavage of the directing group, making it a quite easily scalable approach to access unprotected indoles with high step economy. The DGauto strategy was also applicable for isoquinoline synthesis. In addition, synthetic utilities of this chemistry for rapid assembly of π-extended nitrogen-doped polyheterocycles and bioactive molecules were demonstrated. Copyright
Zheng, Liyao,Hua, Ruimao
supporting information
p. 2352 - 2356
(2014/03/21)

Indole synthesis by rhodium(III)-catalyzed hydrazine-directed C-H activation: Redox-neutral and traceless by N-N bond cleavage
Fishing for complements! There is an alternative to the useful Fischer indole synthesis. The new method utilizes the same retrosynthetic disconnection but is based on a RhIII-catalyzed directed C-H activation step and a successive coupling with alkynes. Copyright
Zhao, Dongbing,Shi, Zhuangzhi,Glorius, Frank
p. 12426 - 12429
(2013/12/04)

General and efficient synthesis of indoles through triazene-directed c-h annulation
Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl-alkyl and alkyl-alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring-contraction-triggered N-N bond cleavage. It allows rapid conversion of the reaction products into several functional molecules. Copyright
Wang, Chengming,Sun, Huan,Fang, Yan,Huang, Yong
p. 5795 - 5798
(2013/06/27)

One-pot-one-step, microwave-assisted Fischer indole synthesis
The Fischer indole synthesis was carried out using microwaves instead of conventional heating procedures. When the mixture of phenylhydrazine, cyclohexanone and zinc chloride was irradiated at 600 W for 3 min, 76% of 1,2,3,4-tetrahydrocarbazole was obtained. However, when zinc chloride was replaced with p-toluenesulfonic acid (p-TSA), the reaction yielded 91% of 1,2,3,4-tetrahydrocarbazole. Thus, a series of indoles were prepared using microwaves in the presence of p-TSA catalyst.
Creencia, Evelyn Cuevas,Tsukamoto, Masayuki,Horaguchi, Takaaki
experimental part
p. 1095 - 1102
(2011/11/04)

Larock heteroannulation of 2-bromoanilines with internal alkynes via ligand and salt free Pd/C catalysed reaction
An alternative to the use of ligands and homogeneous catalysis to promote the synthesis of 2,3-disubstituted indoles starting from 2-bromoanilines is described for the first time. This reaction could be achieved through a Larock heteroannulation via a ligand free heterogeneous catalysis.
Batail, Nelly,Dufaud, Véronique,Djakovitch, Laurent
experimental part
p. 1916 - 1918
(2011/04/22)

SmI2 mediated synthesis of 2,3-disubstituted indole derivatives
A novel preparation of 2,3-disubstituted indole derivatives was achieved through SmI2 induced intramolecular reductive coupling reactions of acylamido carbonyl compounds.
Fan, Xuesen,Zhang, Yongmin
p. 1917 - 1923
(2007/10/03)

Facile preparation of 2,3-disubstituted indole derivatives through low-valent titanium induced intramolecular reductive coupling reactions of acylamido-carbonyl compounds
An efficient synthesis of 2,3-disubstituted indole derivatives through low-valent titanium induced reductive cyclisation of suitably substituted acylamido-carbonyl compounds is described.
Fan, Xuesen,Zhang, Xinying
p. 696 - 697
(2007/10/03)

Indole compounds and their use as estrogen agonists/antagonists
This invention relates to compounds, in particular indoles, that are useful as estrogen agonists and antagonists and pharmaceutical uses thereof. The present invention also relates to indoles that are selective for the ERβ receptor and pharmaceutical uses
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(2008/06/13)

Synthesis and pharmacological activity of some 2,3-diphenylindole derivatives
2,3-Diphenyl-5-methoxyindole-6-carboxaldehyde 2b is reacted with semicarbazide hydrochloride to give the corresponding semicarbazide derivative 3 which is cyclized to the triazole 4. The chalcones 5a and 5b have been prepared from the 5-hydroxy- and 5-methoxyindole derivatives 2a and 2b respectively by treatment with p-aminoacetophenone and these are then cyclized with hydrazine hydrate to 6a and 6b respectively. 5-Chloro-2,3-diphenylindole 7 is converted into the 6-amino derivative 8 by nitration followed by reduction and the amino derivative is then condensed with salicylaldehyde to give the benzoxazepinyl derivative 9. Compound 8 on treatment with acetonitrile, ethyl isothiocyanate and o-chlorophenol yields 10, 11 and 12 respectively. Compounds 1a and 3 are found to be the more potent antiinflammatory compounds compared to indomethacin and 3 and 5b have been found to be more potent than aspirin.
Ismail, M. M. F.,Shmeiss, N. A. M. M.,El-Diwani, H. I.,Arbid, M. S.
p. 288 - 292
(2007/10/03)

SUBSTITUENT INFLUENCE ON THE INDOLIZATION WITH PCl3 OF SOME o,m,p-SUBSTITUTED PHENYLHYDRAZONES
The indolization of deoxybenzoin o,m,p (Me, MeO, Cl), p-NO2 and m-EtO-phenylhydrazones (1) by the above reaction has been examined.All the reactions are carried out at room temperature and high yields of the corresponding indoles (2) are obtained even whe
Baccolini, Graziano,Marotta, Emanuela
p. 4615 - 4620
(2007/10/02)

Cobalt Assisted Synthesis of Indoles from Alkynes and Diaryldiazenes
Co(Cl)(PPh3)3 induces formation of 1/1 adducts (indoles) from alkynes and diaryldiazenes while Co(N2)(PPh3)3 gives rise to 2/1 adducts, respectively. - Keywords: Metal Assisted Organic Synthesis, Heterocycles
Gstach, H.,Kisch, H.
p. 251 - 252
(2007/10/02)