- Synthesis of N-protected/free indole-7-carboxaldehyde
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A direct method for the preparation of N-protected/free indole-7-carboxaldehyde is reported from the corresponding N-protected 7-bromomethylindoles using three different conditions. Copyright Taylor & Francis Group, LLC.
- Mohanakrishnan, Arasambattu K.,Balamurugan, Ramalingam,Ramesh, Neelamegam,Mathiselvam, Manoharan,Manavalan, Subramaniam
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- Design of schiff base-like postmetallocene catalytic systems for polymerization of olefins: IV. Synthesis of 2-(aryliminomethyl)-pyrrole and 7-(aryliminomethyl)indole derivatives containing cycloalkyl substituents
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Reactions of 4,6-substituted 2-cycloalkylanilines with 1H-pyrrole-2- carbaldehyde and 1H-indole-7-carbaldehyde in methanol in the presence of formic acid gave the corresponding Schiff bases which can be used as ligands for titanium and zirconium complexes
- Kochnev,Oleinik,Oleinik,Ivanchev,Tolstikov
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- Enantioselective N-Heterocyclic Carbene-Catalyzed Cascade Reaction for the Synthesis of Pyrroloquinolines via N-H Functionalization of Indoles
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Functionalization of the indole N-H bond for enantioselective synthesis of biologically important pyrroloquinoline derivatives has been reported under oxidative N-heterocyclic carbene catalysis conditions. The interception of catalytically generated chiral α,β-unsaturated acylazoliums with the indole derivatives proceeds in an aza-Michael/Michael/lactonization sequence to deliver the pyrroloquinoline derivatives in good yields, diastereoselectivities, and enantioselectivities. The simultaneous enhancement of reactivity and selectivity observed in polar aprotic solvents is noteworthy.
- Mukherjee, Subrata,Shee, Sayan,Poisson, Thomas,Besset, Tatiana,Biju, Akkattu T.
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- Phosphine-Mediated Sequential [2+4]/[2+3] Annulation to Construct Pyrroloquinolines
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A domino [2+4]/[2+3] sequential annulation reaction of MBH carbonates with N-unprotected indoles has been developed to provide various pyrroloquinoline derivatives in ≤94% yield and 20:1 dr. The reaction could be either mediated by stoichiometric PCy3 or catalyzed by R3PO via PIII/PV O redox cycling in the presence of phenylsilane. This method assembles polycyclic 1,7-fused indoles in one step diastereoselectively.
- Lin, Junhui,Zhu, Yannan,Cai, Wei,Huang, You
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p. 1593 - 1597
(2022/03/03)
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- Piperidine compound and preparation method and medical application thereof
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The invention discloses a piperidine compound shown as a formula (I) and a preparation method and medical application thereof, and particularly relates to a piperidine USP7 inhibitor compound or pharmaceutically acceptable salt or ester or solvate thereof and a preparation method and application of the piperidine USP7 inhibitor compound or pharmaceutically acceptable salt or ester or solvate thereof. The compound provided by the invention can inhibit the activity of USP7 enzyme, has very good selectivity and druggability, and can be used for preparing medicines for preventing or treating tumor diseases or virus infectious diseases.
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- Ruthenium(II)-Catalyzed Highly Chemo- And Regioselective Oxidative C6 Alkenylation of Indole-7-carboxamides
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We disclosed the first efficient method for highly chemo- and regioselective C6 alkenylation of indole-7-carboxamides using inexpensive Ru(II) catalyst through chelation assisted C-H bond activation. Electronically diverse indole-7-carboxamides and alkenes react efficiently to produce a wide range of C6 alkenyl indole derivatives. Further the C6 alkenyl indole-7-carboxamides modified to their derivatives through simple chemical transformations. The observed regioselectivity and kinetics has been evidenced by deuterium incorporation and intermolecular competitive studies. In addition, for mechanistic insights, the intermediates were analyzed by HRMS.
- Jadhav, Pankaj P.,Kahar, Nilesh M.,Dawande, Sudam G.
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p. 8673 - 8677
(2021/11/20)
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- A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered: N -sulfonyl-1,2,3-triazoles and indoles
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An efficient and convenient protocol for the synthesis of a novel class of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles has been disclosed. The reaction proceeds via denitrogenative aza-vinyl rhodium carbene formation to give a carbonyl ylide, which with indole results in 1,3-dipolar cycloaddition followed by sequential semipinacol rearrangement/ring expansion/oxidation to produce azepino fused diindoles. The reaction shows a broad substrate scope giving up to 81% yield. Furthermore, reversible catalytic hydrogenation and photophysical studies were carried out to demonstrate the application of these molecules.
- Kahar, Nilesh,Jadhav, Pankaj,Reddy, R. V. Ramana,Dawande, Sudam
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p. 1207 - 1210
(2020/02/04)
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- Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles
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We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1–1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.
- Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
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supporting information
p. 14167 - 14172
(2017/10/16)
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- Aminocatalyzed Cascade Synthesis of Enantioenriched 1,7-Annulated Indoles from Indole-7-Carbaldehyde Derivatives and α,β-Unsaturated Aldehydes
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We report herein a new cascade strategy for the enantioselective synthesis of 1,7-annulated indoles based on iminium-enamine activation. A careful study of the indole substitution pattern revealed that a chloro substituent at the C-3 position was importan
- Giardinetti, Maxime,Moreau, Xavier,Coeffard, Vincent,Greck, Christine
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p. 3501 - 3506
(2016/01/25)
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- 5-Oxo-ETE receptor antagonists
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5-Oxo-ETE is the most powerful eosinophil chemoattractant among lipid mediators. Eosinophil infiltration into the lungs of asthmatics may be responsible for the late phase of inflammatory asthma. We have designed and synthesized a 5-oxo-ETE receptor antagonist, the purpose of which is to prevent eosinophil migration to the lung during an asthma attack and thereby reduce asthma symptoms.
- Gore, Vivek,Patel, Pranav,Chang, Chih-Tsung,Sivendran, Sashikala,Kang, Namin,Ouedraogo, Yannick P.,Gravel, Sylvie,Powell, William S.,Rokach, Joshua
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p. 3725 - 3732
(2013/06/27)
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- Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region
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A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome.
- Lo, Ho Yin,Nemoto, Peter A.,Kim, Jin Mi,Hao, Ming-Hong,Qian, Kevin C.,Farrow, Neil A.,Albaugh, Daniel R.,Fowler, Danielle M.,Schneiderman, Richard D.,Michael August,Martin, Leslie,Hill-Drzewi, Melissa,Pullen, Steven S.,Takahashi, Hidenori,De Lombaert, Stephane
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p. 4533 - 4539
(2011/09/12)
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- Asymmetric synthesis of highly substituted azapolycyclic compounds via 2-alkenyl sulfoximines: Potential scaffolds for peptide mimetics
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The application of metalated, enantiomerically pure acyclic and cyclic 2-alkenyl sulfoximines for the synthesis of highly substituted aza(poly)cyclic ring systems is described. The method relies on a one-pot combination of a reagent-controlled allyl transfer reaction to α- or β-amino aldehydes, followed by a Michael-type cyclization of the intermediate vinyl sulfoximines generated in the first step. The sulfur-free target compounds are preferentially obtained by samarium iodide treatment of the sulfonimidoyl substituted heterocycles. In addition to this methodological work, initial results on the biological activity of selected examples are reported. Furthermore, a concept for the transformation of peptidic lead structures into non-peptide mimetics is described, and the relevance of the new approach to highly substituted azaheterocycles in this context is discussed.
- Reggelin, Michael,Junker, Bernd,Heinrich, Timo,Slavik, Stefan,Buehle, Philipp
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p. 4023 - 4034
(2007/10/03)
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- Simple synthesis of 7-formyl-indole
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A simple route to 7-formyl-indole (5) is described in which appropriately functionalized o-nitrotoluenes (1) are converted to 7-hydroxymethyl-indole (4) using the Batcho-Leimgruber process. Condensation of 3-methyl-2-nitrobenzyl alcohol (1a) with N,N-dimethylformamide dimethyl acetal yields the enamine 2a, which upon catalytic hydrogenation affords 4 in 22% yield. When the hydroxyl function in 1 is protected with pivaloyl or tetrahydropyranyl group, the yields of 4 are increased to 39% and 48%, respectively. Finally, 4 is oxidized with pyridinium chlorochromate (PCC) to afford 5 in 86% yield. Copyright Taylor & Francis Group, LLC.
- Uchil, Vinod R.,Gund, Machhindra,Satyam, Apparao
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p. 1051 - 1056
(2007/10/03)
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- Sulfonamide peri-substituted bicyclics for occlusive artery disease
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Acyl sulfonamide, peri-substituted, fused bicyclic ring compounds useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed. The compounds are of the general formula A representative example is:
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(2008/06/13)
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- CARBOXYLIC ACID PERI - SUBSTITUTED BICYCLICS FOR OCCLUSIVE ARTERY DISEASE
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Peri-substituted, fused bicyclic ring carboxylic acids useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed.
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Page/Page column 78; 106-107
(2010/11/08)
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- N-benzyl dihydroindole LTD4 antagonists
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This invention relates to pharmaceutical N-benzyl dihydroindole compounds having the general formula: STR1 and their use as LTD4 antagonists.
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- Certain indole derivatives useful as leukotriene antagonists
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A compound of the formula STR1 in which R1 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C1-4 alkyl, aldehydo, --CH2 Z, --CH=CH--Z or --CH2 CH2 Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or --CONR7 R8 where R7 and R8 are each hydrogen or C1-4 alkyl; R3 and R4 are each hydrogen, C1-4 alkyl, optionally substituted phenyl, or C1-4 alkyl substituted by --CONR7 R8 or an optionally protected acid group; R5 is STR2 where W is --CH=CH--, --CH=N--, --N=CH--, --O-- or --S--, R9 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy or trihalomethyl, and R10 is hydrogen, C1-4 alkyl, C2-6 alkenyl, C3-6 cycloalkyl or C1-4 alkyl-C3-6 cycloalkyl; R6 is hydrogen or C1-4 alkyl; X is --O--(CH2)n CR11 R12, --CR11 R12 --, --CR11 R12.(CH2)n.CR13 R14 -- or --CR11 =CR12 -- where R11, R12, R13 and R14 are each hydrogen or C1-4 alkyl, and n is 0, 1 or 2; and Y is --O--CR15 R16 --, --CR15 =CR16 -- or --CR15 R16.CR17 R18 -- where R15, R16, R17 and R18 are each hydrogen or C 1-4 alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.
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- N-Benzyl-Indoles, processes for their preparation and pharmaceutical compositions containing them
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A compound of the formula in which R1 is hydrogen, halo, C??? alkyl, C??? alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C??? alkyl, aldehydo,-CH?Z,-CH=CH-Z or-CH?CH?Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or-CONR?R? where R? and R? are each hydrogen or C??? alkyl, R3 and R? are each hydrogen, C??? alkyl, optionally substituted phenyl, or C??? alkyl substituted by-CONR?R? or an optionally protected acid group; R? is where W is-CH=CH-,-CH=N-,-N=CH-,-O-or-S-, R? is hydrogen, halo, C??? alkyl, C? ?? alkoxy or trihalomethyl, and R1? is hydrogen, C? ?? alkyl, C??? alkenyl, C??? cycloalkyl or C??? alkyl-C??? cycloalkyl; R? is hydrogen or C??? alkyl; X is-O-(CH?)nCR11CR12-,-CR11R12-,-CR11R12.(CH?) n.CR13R1?-or-CR11=CR12-where R11, R12, R13 and R1? are each hydrogen or C??? alkyl, and n is 0, 1 or 2; and Y is-O-CR1?R1?-,-CR1?=CR1?-or-CR1? R1?.CR1?R1?-where R1?, R1?, R1? and R1? are each hydrogen or C??? alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.
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- Metal-Halogen Exchange of Bromoindoles. A Route to Substituted Indoles
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The 4-, 5-, 6-, and 7-bromoindoles, conveniently synthesized by the Batcho-Leimgruber process, serve as efficient precursors to regiochemically pure lithiated indoles.Metal-halogen exchange was most effective if potassium hydride was used first to remove the acidic indole NH, and tert-butyllithium was used then to effect metal-halogen exchange.The resulting indolyl organometallic reagents react with a variety of electrophiles to give regioisomerically pure acylated indoles.
- Moyer, Mikel P.,Shiurba, John F.,Rapoport, Henry
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p. 5106 - 5110
(2007/10/02)
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- The Chemistry of Indoles. XXXIII. Substituent Effect in Regioselective Metalation of 3-Indolecarbaldehyde and Syntheses of Indoles Carrying a Carbon Side Chain at the 4-, 5-, 6-, or 7-Position
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The nature of a substituent on the pyrrole ring of 3-indolecarbaldehyde plays a significant role in governing the regioselectivity of metalation.To confirm the structures of the products, various indoles carrying a carbon side chain at the 4-, 5-, 6-, or 7-position were prepared by other methods.Synthesis of 5-substituted 1-hydroxyindoles is also described.Keywords-thallation; mercuration; 4-substituted indole; 5-substituted indole; 6-substituted indole; 7-substituted indole; regioselective metalation; 3-indolecarbaldehyde; thallation-palladation; 1-hydroxyindole
- Somei, Masanori,Saida, Yoshihiro,Komura, Naoko
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p. 4116 - 4125
(2007/10/02)
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- Nickel(II) Complexes of Imine Ligands derived from 7-Formylindoles
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Quadridentate bis-imine nickel(II) complexes have been formed from 7-formylindoles and 1,2-diaminobenzene: an X-ray crystal structure determination of the chloroform solvate of the N,N'-bis(4,6-dimethoxyindol-7-ylidene)-1,2-diaminobenzene complex shows severe distortion from planarity and a distance of 2.96 Angstroem between the C-2 indole atoms.
- Black, David St C.,Craig, Donald C.,Kumar, Naresh,Wong, Laurence C. H.
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p. 1172 - 1173
(2007/10/02)
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