cas 51417-51-7, 7-Bromoindole | Articles data

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7-Pyridylindoles: Synthesis, structure, and properties
(Chemical Equation Presented) A series of three isomeric 7-pyridylindoles (7-PIs) are prepared where the pyridine attachment is through C2, C3, or C4. These systems are prepared by a combination of the Bartoli reaction and the Stille coupling with an appropriate pyridyl stannane. By treatment with CH 3I, the 7-PIs can be converted to their pyridinium salts. Deprotonation at the NH of these salts leads to a zwitterion which, in the 4-pyridyl system, also exists as a neutral isomer. The photophysical and NMR properties of these systems are discussed. All three pyridylindoles are analyzed by X-ray crystallography and shown to exist in different states of aggregation dictated by the formation of intra- and intermolecular H-bonds.
Mudadu, Maria Salvatora,Singh, Ajay,Thummel, Randolph P.
p. 7611 - 7617
(2006)
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A short synthesis of hippadine
A synthesis of the pyrrolophenanthridone alkaloid hippadine is described. The approach features the use of a low temperature Ullman type coupling reaction to effect construction of the pentacyclic skeleton and an unusual methylene oxidation promoted by barium manganate.
Harrowven, David C.,Lai, Darren,Lucas, Matthew C.
p. 1300 - 1302
(1999)
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CONDENSED HETEROAROMATIC RING SYSTEMS. XXIII. A CONCISE SYNTHESIS OF HIPPADINE
Hippadine, a pyrrolophenanthridine alkaloid, was synthesized in 39percent overall yield of three steps using the palladium-catalyzed cross-coupling reaction of 2,6-dibromoaniline with (Z)-1-tributylstannyl-2-ethoxyethene as a key step.
Sakamoto, Takao,Yasuhara, Akito,Kondo, Yoshinori,Yamanaka, Hiroshi
p. 2597 - 2600
(1993)
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Rh(III)-Catalyzed Selective C7 Halogenation of Indolines
An efficient Rh-catalyzed catalytic method has been developed for selective C7 halogenation of N-pyrimidyl indolines with N-halosuccinimides (Cl, Br, I) to produce corresponding halides in good to excellent yields. The advantages of this strategy include
Manisha,Gupta, Shiv Shankar,Dhiman, Ankit Kumar,Sharma, Upendra
p. 5443 - 5448
(2021/10/25)

Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo
Indigoids represent natural product-based compounds applicable as organic semiconductors and photoresponsive materials. Yet modified indigo derivatives are difficult to access by chemical synthesis. A biocatalytic approach applying several consecutive selective C?H functionalizations was developed that selectively provides access to various indigoids: Enzymatic halogenation of l-tryptophan followed by indole generation with tryptophanase yields 5-, 6- and 7-bromoindoles. Subsequent hydroxylation using a flavin monooxygenase furnishes dibromoindigo that is derivatized by acylation. This four-step one-pot cascade gives dibromoindigo in good isolated yields. Moreover, the halogen substituent allows for late-stage diversification by cross-coupling directly performed in the crude mixture, thus enabling synthesis of a small set of 6,6’-diarylindigo derivatives. This chemoenzymatic approach provides a modular platform towards novel indigoids with attractive spectral properties.
Schnepel, Christian,Dodero, Veronica I.,Sewald, Norbert
supporting information
p. 5404 - 5411
(2021/03/03)

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations
Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.
Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo
supporting information
p. 7738 - 7744
(2021/05/07)

Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group
Pd-catalyzed directing-group-assisted regioselective halogenations to C7 of indolines and C8 of tetrahydroquinolines were achieved in good to excellent yields. The practicality and utility of the developed method have been illustrated by various functiona
Ahmad, Ashfaq,Dutta, Himangsu Sekhar,Kumar, Mohit,Khan, Afsar Ali,Raziullah,Koley, Dipankar
p. 5870 - 5875
(2020/07/30)

Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring
Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).
Qiang-Liu,Liu, Yu-Xiu,Song, Hong-Jian,Wang, Qing-Min
supporting information
p. 3110 - 3115
(2020/07/04)

Synthesis of 7-halo indoles (by machine translation)
The present invention relates to synthesis of 7? Halo indole method, comprising the steps of:O-halogenated aniline, chloral hydrate and hydroxylamine hydrochloride by the Sandmeyer reaction to synthesize 7? halogenating isatin ; 7? halogenating isatin dissolved with an organic solvent, in the reducing agent by reduction reaction under the conditions of 7? Halo indole, the reducing agent is an alkali metal borohydride system, four system adopts, lithium hydride system or triethyl silane system. The beneficial effect of the invention is:in order to O-halogenated aniline and the chloral hydrate is, hydroxylamine hydrochloride as raw materials, by the Sandmeyer shall synthesis method for preparing compositions b isonitroso 7? halogenating isatin, and then by further reduction and system reduction to prepare 7? Halo indole; by the 7? Preparation halogenating isatin 7? Halo indole method, the raw material is easy to obtain, low price, higher process yield, the product purity is good, simple operation, and the like, is suitable for batch preparation 7? Halo indole. (by machine translation)
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(2017/01/12)

A 1 - (phenyl) - 2, 3, 4, 9-tetrahydro -1H-pyrido [3,4-b] indole derivatives thereof in the preparation of the application of the anti-tumor drug (by machine translation)
The invention belongs to the technical field of pharmaceutical chemistry, in particular to a kind of 1 - (phenyl) - 2, 3, 4, 9-tetrahydro -1H-pyrido [3,4-b] indole derivatives thereof in the preparation of the application of the anti-tumor drugs. Research display inhibit one or more prostandin receptor activity can be effective for the treatment of hypertension, at least one kind of prostagladin E2 receptor in the blood pressure regulating system RAAS in the course of play a crucial role, we by changing 1 and 8 is the angle of the two groups and the distance to EP3 receptor research, we developed a new high-efficiency of the synthetic route to study a series of derivatives, all of the target compound are all new product, all of the compound through the nuclear magnetic resonance and quality of the identification of the structure. The target compound in the antibacterial, anti-tumor, analgesic, anti-platelet aggregation, the promotion of kidney part of the reabsorption of sodium and water, regulating neurotransmitter release, promote adipose tissue Lipolysis and has an important role of anti-arrhythmia. (by machine translation)
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Paragraph 0071-0073

(2016/11/14)

Synthesis of phenanthridine skeletal Amaryllidaceae alkaloids
Strategies for the synthesis of Amaryllidaceae alkaloids, including crinasiadine, trisphaeridine, bicolorine, N-methylcrinasiadine, 5,6-dihydrobicolorine, galanthindole, lycosinine A and lycosinine B were reported. Investigation of optionally synthetic routes to approach bicolorine, 5,6-dihydrobicolorine, trisphaeridine and N-methylcrinasiadine were demonstrated as well. In addition, three structurally related alkaloids galanthindole, lycosinine A and lycosinine B were concisely prepared by using Suzuki coupling reaction as the key step.
Fan-Chiang, Tai-Ting,Wang, Hung-Kai,Hsieh, Jen-Chieh
p. 5640 - 5645
(2016/08/17)

Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement
A short formal total synthesis of the marine natural product diazonamide A is described. The route is based on indole oxidative rearrangement, and a number of options were investigated involving migration of tyrosine or oxazole fragments upon oxidation of open chain or macrocyclic precursors. The final route proceeds from 7-bromoindole by sequential palladium-catalysed couplings of an oxazole fragment at C-2, followed by a tyrosine fragment at C-3. With the key 2,3-disubstituted indole readily in hand, formation of a macrocyclic lactam set the stage for the crucial oxidative rearrangement to a 3,3-disubstituted oxindole. Notwithstanding the concomitant formation of the unwanted indoxyl isomer, the synthesis successfully delivered, after deprotection, the key oxindole intermediate, thereby completing a formal total synthesis of diazonamide A.
David, Nadège,Pasceri, Raffaele,Kitson, Russell R. A.,Pradal, Alexandre,Moody, Christopher J.
supporting information
p. 10867 - 10876
(2016/07/27)

One-pot construction of 3,3′-bisindolylmethanes through Bartoli indole synthesis
A one-pot approach to 3,3′-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3′-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH 4Cl.
Abe, Takumi,Nakamura, Shuuhei,Yanada, Reiko,Choshi, Tominari,Hibino, Satoshi,Ishikura, Minoru
p. 3622 - 3625
(2013/08/23)

Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B
Vinylindoles undergo Ni(II)-catalyzed asymmetric hydrovinylation under very mild conditions (-78 °C, 1 atm ethylene, 4 mol % catalyst) to give the corresponding 2-but-3-enyl derivatives in excellent yields and enantioselectivities. Hydroboration of the alkene and oxidation to an acid, followed by Friedel-Crafts annulation, gives an indole-annulated cyclopentanone that is a suitable precursor for the syntheses of cis-trikentrins and all known herbindoles. For example, the cyclopentanone from 4-ethyl-7-vinylindole is converted into (+)-cis-trikentin A in four steps (Wittig reaction, alkene isomerization, diastereoselective hydrogenation, and nitrogen deprotection). The previous synthesis of this molecule from (S)-(-)-malic acid involved more than 20 steps and a preparative HPLC separation of diastereomeric intermediates.
Liu, Wang,Lim, Hwan Jung,Rajanbabu
supporting information; experimental part
p. 5496 - 5499
(2012/05/20)

Novel achiral indole-substituted titanocenes: Synthesis and preliminary cytotoxicity studies
A series of eight new titanocene dichloride derivatives has been synthesised and characterized. Four compounds from the series are lypophilic indole-functionalised titanocenes and four are hydrochloride salts of their dimethylaminomethyl-functionalised counterparts, which are water soluble. The compounds were tested for their in vitro cytotoxicities against the human kidney cancer cell line CAKI-1 and their results are compared with previously synthesised structural analogues. Surprisingly, two of the compounds showed no activity against the CAKI-1 cell line; however six compounds exhibited medium to high potency with IC50 values as low as 7.0 μM. These six complexes were tested further on this cell line using the co-solvent Soluphor P, which has been shown to improve both solubility and cytotoxicity of similar complexes. One of the compounds carrying a N-methylindole-substituent was obtained in the form of single crystals and allowed for the characterisation by X-ray crystallography; the compound crystallised in the space group P21/n (#14) with four molecules present in the monoclinic unit cell.
Deally, Anthony,Gleeson, Brendan,Müller-Bunz, Helge,Patil, Siddappa,O'Shea, Donal F.,Tacke, Matthias
scheme or table
p. 1072 - 1083
(2011/04/25)

Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles
Chemical Figure Presented Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The lr-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthrldone class of alkaloid natural products. Copyright
Robbins, Daniel W.,Boebel, Timothy A.,Hartwig, John F.
supporting information; experimental part
p. 4068 - 4069
(2010/05/01)

A novel, air-stable phosphine ligand for the palladium-catalyzed suzuki-miyaura cross-coupling reaction of chloro arenes
(Figure presented) A novel, air-stable phosphine ligand, prepared from readily available 2-bromonitrobenzene and vinylmagnesium bromide, combines with Pd(CH3CN)2Cl2 to afford an effective catalyst for Suzuki-Miyaura cross-coupling of aryl, heteroaryl, and allyl chlorides with phenylboronic acid.
Ghosh, Raju,Adarsh,Sarkar, Amitabha
scheme or table
p. 5320 - 5322
(2010/10/19)

DIAZONAMIDE ANALOGS
Novel diazonamide analogs having anti-mitotic activity, useful for the treatment of cancer and other proliferative disorders are provided.
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Page/Page column 48-49

(2009/12/27)

DIAZONAMIDE ANALOGS WITH IMPROVED SOLUBILITY
Diazonamide A analogs, and the salts, esters and conjugates thereof, having improved aqueous solubility are provided. Also provided are pharmaceutical compositions, and methods for preparing and using such compounds and compositions for the treatment of proliferative diseases.
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Page/Page column 21

(2009/07/10)

7-SUBSTITUTED INDOLE MCL-1 INHIBITORS
Compounds which inhibit the activity of anti-apoptotic Mcl-1 protein, compositions containing the compounds, and methods of treating diseases involving overexpressed or unregulated Mcl-1 protein are disclosed
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Page/Page column 166

(2008/12/08)

Indole diterpene synthetic studies: Development of a second-generation synthetic strategy for (+)-nodulisporic acids A and B
(Chemical Equation Presented) A second-generation strategy for construction of (+)-nodulisporic acids A and B based on the development of a new, effective modular indole synthesis exploiting a sequential Stille cross-coupling/Buchwald- Hartwig union/cyclization tactic is disclosed. This strategy evolved due to the considerable acid instability of the C(24) hydroxyl group observed in several advanced intermediates during our first-generation approach.
Smith III, Amos B.,Kuerti, Laszlo,Davulcu, Akin H.,Young, Shin Cho,Ohmoto, Kazuyuki
p. 4611 - 4620
(2008/02/07)

CRYSTAL OF TWO-RING HETEROCYCLIC SULFONAMIDE COMPOUND
Novel β-type crystal of N-(3-chloro-1H-indol-7-yl)-4-sulfamoylbenzenesulfonamide of the formula: characterized in, for example, that in powder X-ray diffractometry, it has a diffraction peak at a diffraction angle (2θ±0.2°) of 18.4°. This crystal has favorable properties, such as high solubility in buffer solutions and various organic solvents, and is suitable to an active ingredient of a pharmaceutical composition for use as an antitumor agent, an activated lymphocyte suppressor or an eating enhancer.
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Page/Page column 6

(2008/06/13)

Preparation of 7-halo-indoles by thallation of N-formylindoline and their attempted use for synthesis of the right-hand segment of chloropeptin
7-Substituted (Cl, Br, I) indoles were synthesized by using thallation of N-formylindoline as a key reaction. Two precursor tripeptides for the right-hand segment of chloropeptin were synthesized by using (R)-7′-iodo and 7′-bromotryptophans derived from each 7-substituted indole (I, Br) obtained by the above procedure.
Yamada, Yaeko,Arima, Shiho,Okada, Chiharu,Akiba, Ai,Kai, Toshitsugu,Harigaya, Yoshihiro
p. 788 - 794
(2007/10/03)

A new modular indole synthesis. Construction of the highly strained CDEF parent tetracycle of nodulisporic acids A and B
Construction of the highly strained CDEF parent tetracycle, a structural motif found only in the potent ectoparasiticidal agents (+)-nodulisporic acids A and B and related congeners, has been achieved via a new modular indole synthesis, exploiting a sequential Stille cross-coupling/Buchwald-Hartwig union/cyclization tactic. The new indole synthesis holds the promise of rapid assembly of diverse, highly substituted indoles possessing uncommon substitution patterns.
Smith III, Amos B.,Kuerti, Laszlo,Davulcu, Akin H.
p. 2167 - 2170
(2007/10/03)

Use of indole-3-acetic acid derivatives in medicine
Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R′3 are independently selected from II or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups lower alkoxy groups, aryl groups or aryloxy groups, wherein it least one of R4, R5, R6, and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT
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(2008/06/13)

Indole-3-acetic acid derivatives
Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R′3 are independently selected from H or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups, lower alkoxy groups, aryl groups or aryloxy groups, wherein at least one of R4, R5, R6 and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT.
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(2008/06/13)

USE OF INDOLE-3-ACETIC ACID DERIVATIVES IN MEDICINE
Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R'3 are independently selected from II or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups lower alkoxy groups, aryl groups or aryloxy groups, wherein it least one of R4, R5, R6, and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT
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(2008/06/13)

Chemistry and biology of diazonamide A: First total synthesis and confirmation of the true structure
With the addition of a tenth ring, the exchange of an oxygen atom for a nitrogen in the heart of the molecule, and a different terminal residue, the revised architecture for diazonamide A (1) provided an even more challenging molecular puzzle for chemical synthesis than its predecessor. In this article, we detail the first successful total synthesis of diazonamide A, an endeavor which not only verified its proper connectivities and established the stereochemistry of its previously unassignable C-37 chiral center, but which also was attended by the development of several new synthetic strategies and tactics.
Nicolaou,Chen, David Y.-K.,Huang, Xianhai,Ling, Taotao,Bella, Marco,Snyder, Scott A.
p. 12888 - 12896
(2007/10/03)

Integrin expression inhibitors
The present invention provides an integrin expression inhibitor, and an agent for treating arterial sclerosis, psoriasis, cancer, retinal angiogenesis, diabetic retinopathy or inflammatory diseases, an anticoagulant, or a cancer metastasis suppressor on the basis of an integrin inhibitory action. Namely, it provides an integrin expression inhibitor comprising, as an active ingredient, a sulfonamide compound represented by the following formula (I), a pharmacologically acceptable salt thereof or a hydrate of them. In the formula, B means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated; K means a single bond, —CH═CH— or —(CR4bR5b)mb— (wherein R4b and R5b are the same as or different from each other and each means hydrogen atom or a C1-C4 alkyl group; and mb means an integer of 1 or 2); R1 means hydrogen atom or a C1-C6 alkyl group; Z means a single bond or —CO—NH—; and R means a C6-C10 aryl ring or 6- to 10-membered heteroaryl ring which may have a substituent and in which a part of the ring may be saturated, respectively.
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(2008/06/13)

Synthesis of Macrocyclic Peptide Analogues of Proteasome Inhibitor TMC-95A
The synthesis of three constrained macrocyclic peptide analogues 1 of TMC-95A as potential proteasome inhibitors is described. The key step involves a Ni(O)-mediated macrocyclization of tripeptides 2 bearing halogenated aromatic side chains for the formation of the biaryl junction. In addition, an enantioselective preparation of L-7-bromotryptophan methyl ester 3 using a Corey-O'Donnell alkylation of the glycine benzophenone imine was achieved in good overall yield with very high ee (>85%) on a multigram scale.
Berthelot, Alexandra,Piguel, Sandrine,Le Dour, Gwennael,Vidal, Joelle
p. 9835 - 9838
(2007/10/03)

Convenient synthesis of 7′ and 6′-bromo-D-tryptophan and their derivatives by enzymatic optical resolution using D-aminoacylase
Compounds 7′ and 6′-bromo-D-tryptophan (1 and 2) which are important derivatives for the synthesis of the chloropeptin and kistamycin A, respectively, were conveniently synthesized by optical resolution from N-acetyl-7′ and 6′-bromo-DL-tryptophan ((RS)-5 and (RS)-14) using D-aminoacylase.
Konda-Yamada, Yaeko,Okada, Chiharu,Yoshida, Kiminari,Umeda, Yasuyuki,Arima, Shiho,Sato, Noriko,Kai, Toshitsugu,Takayanagi, Hiroaki,Harigaya, Yoshihiro
p. 7851 - 7861
(2007/10/03)

Total synthesis of indoles from Tricholoma species via Bartoli/heteroaryl radical methodologies
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Dobbs
p. 638 - 641
(2007/10/03)

A focused compound library of novel N-(7-indolyl)benzenesulfonamides for the discovery of potent cell cycle inhibitors
A series of compounds containing an N-(7-indolyl)benzenesulfonamide pharmacophore was synthesized and evaluated as a potential antitumor agent. Cell cycle analysis with P388 murine leukemia cells revealed that there were two different classes of potent cell cycle inhibitors; one disrupted mitosis and the other caused G1 accumulation. Herein described is the SAR summary of the substituent patterns on this pharmacophore template. (C) 2000 Elsevier Science Ltd. All rights reserved.
Owa, Takashi,Okauchi, Tatsuo,Yoshimatsu, Kentaro,Sugi, Naoko Hata,Ozawa, Yoichi,Nagasu, Takeshi,Koyanagi, Nozomu,Okabe, Tadashi,Kitoh, Kyosuke,Yoshino, Hiroshi
p. 1223 - 1226
(2007/10/03)

A concise synthesis of 7-substituted indoles
7-Substituted indoles were synthesized by the basic cyclization of 6-substituted tert-butyl 2-(trimethylsilyiethynyl)phenylcarbamates which were derived by the lithiation of tert-butyl 2- (trimethylsilylethynyl)phenylcarbamate and the subsequent reaction with electrophiles.
Kondo, Yoshinori,Kojima, Satoshi,Sakamoto, Takao
p. 2741 - 2746
(2007/10/03)

The reaction of vinyl Grignard reagents with 2-substituted nitroarenes: A new approach to the synthesis of 7-substituted indoles
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Bartoli,Palmieri,Bosco,Dalpozzo
p. 2129 - 2132
(2007/10/02)

The Chemistry of Indoles. XXXIX. A Facile Synthetic Method for 7-Substituted Indoles
A simple four-step synthetic method for 7-iodo-, 7-bromo- and 7-chloroindole was established with high overall yield starting from 2,3-dihydroindole.Several 7-substituted indoles carrying a carbon side chain and 7-methoxyindole were also synthetized.Keywords - thallation; 7-substituted indole; regioselective metalation; 7-iodoindole; 7-bromoindole; 7-chloroindole; 7-methoxyindole; methyl 3-(indol-7-yl)acrylate; 4-(indol-7-yl)-2-methyl-3-buten-2-ol; Heck reaction
Somei, Masanori,Saida, Yoshihiro,Funamoto, Tetsuo,Ohta, Toshihara
p. 3146 - 3154
(2007/10/02)

Metal-Halogen Exchange of Bromoindoles. A Route to Substituted Indoles
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
p. 5106 - 5110
(2007/10/02)

Studies on Several 7-Substituted N,N-Dimethyltryptamines
Several 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were prepared and evaluated in the rat fundus serotonin receptor assay and in a behavioral (discriminative stimulus) assay in rats.Both 7-Me- and 5-Ome-7-Me-DMT possess a higher pA2, and 5,7-(OMe)2-DMT a lower pA2, than that of DMT itself.Like DMT, all three of these compounds produce behavioral effects in rats which are similar to those of the hallucinogen 5-OMe-DMT.Although 7-Et- and 7-Br-DMT possess a higher serotonin receptor affinity than DMT, neither produce behavioral effects which parallelthose of 5-OMe-DMT.In contrast, 6-OMe-DMT and its 5-OMe derivative do not interact with the serotonin receptors in a competitive manner and are inactive in the discriminative stimulus assay.
Glennon, R. A.,Schubert, E.,Jacyno, J. M.,Rosecrans, J. A.
p. 1222 - 1226
(2007/10/02)