- MUKONICINE, A CARBAZOLE ALKALOID FROM LEAVES OF MURRAYA KOENIGII
-
A new carbazole alkaloid, mukonicine, was isolated from the leaves of Murraya koenigii.From physical methods coupled with chemical evidence its structure was determined as 1,2-3-pyrano>-3-methyl-6,8-dimethoxycarbazole. - Key Word Index: Murraya koenigii; Rutaceae; mukonicine; carbazole alkaloid.
- Mukherjee, M.,Mukherjee, S.,Shaw, A. K.,Ganguly, S. N.
-
-
Read Online
- GLYCOZOLININE, A CARBAZOLE DERIVATIVE FROM GLYCOSMIS PENTAPHYLLA
-
Key Word Index - Glycosmis pentaphylla; Rutaceae; seeds; alkaloids; glycozolinine; carbazole. A new carbazole derivative, glycozolinine, was isolated from the seeds of Glycosmis pentaphylla.From physical and chemical evidence its structure is 6-hydroxy-3-methylcarbazole.
- Mukherjee, S.,Mukherjee, M.,Ganguly, S. N.
-
-
Read Online
- Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst
-
An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.
- Steingruber, H. Sebastián,Mendioroz, Pamela,Volpe, María A.,Gerbino, Darío C.
-
p. 4048 - 4058
(2021/08/03)
-
- Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon-Carbon/Carbon-Nitrogen Bond-Forming Reactions
-
Self-assembled multilayer iron(0) nanoparticles (NPs, 6-10 nm), namely, sulfur-modified Au-supported Fe(0) [SAFe(0)], were developed for ligand-free one-pot carbon-carbon/carbon-nitrogen bond-forming reactions. SAFe(0) was successfully prepared using a well-established metal-nanoparticle catalyst preparative protocol by simultaneous in situ metal NP and nanospace organization (PSSO) with 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (Si-DHP) as a strong reducing agent. SAFe(0) was easy to handle in air and could be recycled with a low iron-leaching rate in reaction cycles.
- Akiyama, Toshiki,Arisawa, Mitsuhiro,Haneoka, Hitoshi,Harada, Kazuo,Hasegawa, Jun-Ya,Honma, Tetsuo,Mashima, Kazushi,Sato, Yoshihiro,Shimoda, Shuhei,Shio, Yasunori,Suzuki, Takeyuki,Tamenori, Yusuke,Tsurugi, Hayato,Tsuruta, Kazuki,Wada, Yuki,Yamada, Makito
-
p. 7244 - 7249
(2020/10/12)
-
- Dearomatization-Rearomatization Strategy for Synthesizing Carbazoles with 2,2′-Biphenols and Ammonia by Dual C(Ar)-OH Bond Cleavages
-
Carbazole is an essential building block in various pharmaceuticals, agrochemicals, natural products, and materials. For future sustainability, it is highly desirable to synthesize carbazole derivatives directly from renewable resources or cheap raw materials. Phenolic compounds are a class of degradation products of lignin. On the other hand, ammonia is a very cheap industrial inorganic chemical. Herein, an efficient dearomatization-rearomatization strategy has been developed to directly cross-couple 2,2′-biphenols with ammonia by dual C(Ar)-OH bond cleavages. This strategy provides a greener pathway to synthesize valuable carbazole derivatives from phenols.
- Cao, Dawei,Yu, Jing,Zeng, Huiying,Li, Chao-Jun
-
p. 13200 - 13205
(2020/12/18)
-
- Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes
-
An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.
- Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
-
p. 15793 - 15798
(2020/10/12)
-
- Substituent-Guided Palladium-Ene Reaction for the Synthesis of Carbazoles and Cyclopenta[ b]indoles
-
An efficient palladium-catalyzed intramolecular Trost-Oppolzer type Alder-ene strategy was developed for the synthesis of carbazoles and cyclopenta[b]indoles from easily accessible(3-allyl-1H-indol-2-yl)methyl acetates. This strategy was extended for the synthesis of naphthalenes and dibenzobenzofurans as well. In addition, a short synthesis of antibacterial and antifungal natural product glycozoline and its analogues was also achieved.
- Yadav, Sonu,Hazra, Raju,Singh, Animesh,Ramasastry
-
-
- Substituent-Guided Palladium-Ene Reaction for the Synthesis of Carbazoles and Cyclopenta[b]indoles
-
An efficient palladium-catalyzed intramolecular Trost-Oppolzer type Alder-ene strategy was developed for the synthesis of carbazoles and cyclopenta[b]indoles from easily accessible(3-allyl-1H-indol-2-yl)methyl acetates. This strategy was extended for the synthesis of naphthalenes and dibenzobenzofurans as well. In addition, a short synthesis of antibacterial and antifungal natural product glycozoline and its analogues was also achieved.
- Yadav, Sonu,Hazra, Raju,Singh, Animesh,Ramasastry
-
supporting information
p. 2983 - 2987
(2019/05/10)
-
- Visible-light-promoted intramolecular C-H amination in aqueous solution: Synthesis of carbazoles
-
An effective and operationally simple protocol is reported for the synthesis of versatile carbazoles. With water as a co-solvent, visible-light rather than various metals is used to facilitate the conversion of readily available 2-azidobiphenyls under mild conditions. Various functionalized bioactive natural alkaloids, such as glycoborine, clausine C, clausine L, clausine H and clauszoline K, were synthesized efficiently with nitrogen as a sole byproduct. The reaction could be performed in water, acidic or alkaline buffer solutions, showing its potential for applications in biochemistry.
- Yang, Lizheng,Zhang, Yipin,Zou, Xiaodong,Lu, Hongjian,Li, Guigen
-
p. 1362 - 1366
(2018/03/26)
-
- Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids
-
An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.
- Dalvi, Bhakti A.,Lokhande, Pradeep D.
-
p. 2145 - 2149
(2018/05/08)
-
- Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate
-
A visible-light-induced synthesis of N-H carbazoles from easily accessible 2,2′-diaminobiaryls in the absence of any external photosensitizer is reported. The process only requires tBuONO and natural resources, visible light, and molecular oxygen for the synthesis of N-H carbazoles. Experimental and computational studies support that the in situ formation of a visible-light-absorbing photosensitizing intermediate, benzocinnoline N-imide, is responsible for the activation of triplet molecular oxygen to singlet oxygen that, in turn, promotes the synthesis of carbazole.
- Chatterjee, Tanmay,Roh, Geum-Bee,Shoaib, Mahbubul Alam,Suhl, Chang-Heon,Kim, Jun Soo,Cho, Cheon-Gyu,Cho, Eun Jin
-
p. 1906 - 1909
(2017/04/11)
-
- Photochemical intramolecular amination for the synthesis of heterocycles
-
Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor. The experimental set-up is tolerant to UV-sensitive functional groups while affording diverse carbazoles, as well as an indole and pyrrole framework, in short reaction times. The photochemical method is presumed to progress through a mechanism differing from the other methods of azide activation involving transition metal catalysis.
- Parisien-Collette, Shawn,Cruché, Corentin,Abel-Snape, Xavier,Collins, Shawn K.
-
p. 4798 - 4803
(2017/10/23)
-
- Synthetic method of carbazole and derivatives thereof
-
The invention discloses a synthetic method of carbazole and derivatives thereof. The synthetic method is characterized in that the carbazole and derivatives thereof are obtained by N-substituted reaction, vinylation reaction, removal of R2 group and olefin closed-loop double decomposition reaction. According to the synthetic method of the carbazole and derivatives thereof, disclosed by the invention, various derivatives of the carbazole can be synthesized according to substituent groups on indole rings of raw materials; in addition, no substituent group is formed on N of the carbazole; the substituent group can be used as an intermediate as required for next-step synthesis. Meanwhile, according to the synthetic method disclosed by the invention, the carbazole and derivatives thereof are synthesized by using the raw materials with abundant sources, and further the huge demand of the carbazole and derivatives thereof is met. Besides, a synthetic route is simple, reaction conditions are easily controlled and realized, the yield of a product is high, and higher practicality is realized.
- -
-
Paragraph 0070; 0071; 0072; 0073; 0074; 0075; 0082-0087
(2017/07/18)
-
- Photochemical C–H Activation: Generation of Indole and Carbazole Libraries, and First Total Synthesis of Clausenawalline D
-
The photolysis of N-aryltriazoles and N-arylbenzotriazoles leads to indoles and carbazoles, respectively. Because libraries of triazoles can be accessed rapidly, for example by the copper-catalyzed [3+2] cycloaddition reaction between alkynes and azides, this reaction allows the preparation of indoles in a single operation, by the simultaneous photolysis of the precursor library. As an example of such a synthesis of carbazoles, we prepared for the first time clausenawalline D, an antimalarial alkaloid that was recently isolated.
- Alimi, Isak,Remy, Richard,Bochet, Christian G.
-
p. 3197 - 3210
(2017/06/21)
-
- A unified strategy for silver-, base-, and oxidant-free direct arylation of C-H bonds
-
Here, we report a dual catalytic approach for room temperature direct arylation of C-H bonds with aryldiazonium salts as a simple aryl group donor, also working as an internal oxidant via C-N2 bond cleavage. This unified strategy has been achieved by the synergistic combination of visible-light metal-free photoredox and palladium catalysis under silver-, base- and/or additive-free conditions. The broad substrate scope, functional group tolerance, excellent regioselectivity and redox-neutral conditions of this process make it attractive for the effective synthesis of a wide range of important N-heterocyclic commodities such as dibenzo[b,d]azepine, carbazole and phenanthridine.
- Sahoo, Manoj K.,Midya, Siba P.,Landge, Vinod G.,Balaraman, Ekambaram
-
p. 2111 - 2117
(2017/07/24)
-
- A Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Route to the Carbazole Natural Products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A
-
The title natural products 2-7 have been prepared by reductive cyclization of the relevant 2-arylcyclohex-2-en-1-one (e.g. 20) to the corresponding tetrahydrocarbazole and dehydrogenation (aromatization) of this to give the target carbazole (e.g. 4). Compounds such as 20 were prepared using a palladium-catalyzed Ullmann cross-coupling reaction between the appropriate 2-iodocyclohex-2-en-1-one and o-halonitrobenzene.
- Yan, Qiao,Gin, Emma,Wasinska-Kalwa, Malgorzata,Banwell, Martin G.,Carr, Paul D.
-
p. 4148 - 4159
(2017/04/27)
-
- Iron-Catalyzed Intramolecular C(sp2)-H Amination
-
The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.
- Alt, Isabel T.,Plietker, Bernd
-
p. 1519 - 1522
(2016/02/14)
-
- Palladium-Catalyzed Intramolecular C–H Amination in Water
-
Palladium(II) catalysis was found to be effective for intramolecular C–H amination in water. With 2-azidobiphenyls as substrates, the reaction efficiently provided various carbazoles with N2as the sole byproduct. The reaction showed high functional-group tolerance and could be used in the synthesis of several natural carbazole alkaloids. The catalytic process was promoted by water, and the reaction was inefficient in the organic solvents that were investigated.
- Yang, Lizheng,Li, Hao,Zhang, Haifei,Lu, Hongjian
-
p. 5611 - 5615
(2016/12/14)
-
- Direct synthesis of N -H carbazoles via iridium(III)-catalyzed intramolecular C-H amination
-
The iridium-catalyzed dehydrogenative cyclization of 2-aminobiphenyls proceeds smoothly in the presence of a copper cocatalyst under air as a terminal oxidant through intramolecular direct C-H amination to produce N-H carbazoles. A similar iridium/copper system can also catalyze the unprecedented dimerization reaction of 2-aminobiphenyl involving 2-fold C-H/N-H couplings.
- Suzuki, Chiharu,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
-
p. 1597 - 1600
(2015/03/30)
-
- One-pot synthesis of carbazoles via tandem C-C cross-coupling and reductive amination
-
We have developed a highly efficient synthetic route to carbazoles that employs sequential C-C/C-N bond formation via Suzuki cross-coupling and Cadogan cyclization using commercially available or easily preparable starting materials. The developed method is compatible with electron neutral, rich or deficient substrates. The synthetic utility of this method was demonstrated by the concise syntheses of four natural products (glycozoline, glycozolicine, glycozolidine and clausenalene).
- Goo, Deuk-Young,Woo, Sang Kook
-
supporting information
p. 122 - 130
(2015/12/30)
-
- KOtBu mediated efficient approach for the synthesis of fused heterocycles via intramolecular O-/N-arylations
-
A novel and efficient methodology for the synthesis of 6H-benzo[c]chromenes, 6H-benzo[c]chromen-6-ones, carbazoles, dibenzofurans, dibenzooxepins has been developed. The reaction goes through intramolecular O-/N-arylations with sp2C-Br bonds via typical SNAr pathway in presence of potassium-tert-butoxide base.
- Singha, Raju,Ahmed, Atiur,Nuree, Yasin,Ghosh, Munmun,Ray, Jayanta K.
-
p. 50174 - 50177
(2015/06/25)
-
- Palladium-catalyzed α-arylation of enones in the synthesis of 2-alkenylindoles and carbazoles
-
A new unified strategy has been developed for the synthesis of substituted 2-alkenylindoles and carbazoles. The strategy uses palladium-catalyzed α-arylation of TES-enol ethers of enones as the key step. The method is highly regioselective, provides good yields, and is expected to have wide application.
- Kale, Ajit Prabhakar,Kumar, Gangam Srikanth,Mangadan, Arun Raj Kizhakkayil,Kapur, Manmohan
-
supporting information
p. 1324 - 1327
(2015/03/14)
-
- "transition-metal-free" synthesis of carbazoles by photostimulated reactions of 2′-halo[1,1′-biphenyl]-2-amines
-
An efficient and simple protocol for the preparation of a series of 9H-carbazoles by photostimulated SRN1 substitution reactions is presented. Substituted 9H-carbazoles were synthesized in low to excellent yields (up to 96%) through an intramolecular C-N bond formation of 2′-halo[1,1′-biphenyl]-2-amines by the photoinitiated SRN1 mechanism under mild and "transition-metal-free" conditions. The biphenylamines used as substrates were obtained with isolated yields ranging from 21% to 84% by two approaches: (A) the cross-coupling Suzuki-Miyaura reaction and (B) the radical arylation of anilines. Some key aspects of the proposed mechanism were evaluated at the B3LYP/6-311+G? level.
- Guerra, Walter D.,Rossi, Roberto A.,Pierini, Adriana B.,Barolo, Silvia M.
-
p. 928 - 941
(2015/01/30)
-
- Iodine-catalyzed aromatization of tetrahydrocarbazoles and its utility in the synthesis of glycozoline and murrayafoline A: A combined experimental and computational investigation
-
A new protocol for the aromatization of tetrahydrocarbazoles has been achieved using a catalytic amount of iodine, giving high yields. The role of iodine in the aromatization has been explained by DFT, and its wide scope is extended to the total synthesis of glycozoline and murrayafoline A. This method has proven to be tolerant of a broad range of functional groups. This journal is the Partner Organisations 2014.
- Humne, Vivek,Dangat, Yuvraj,Vanka, Kumar,Lokhande, Pradeep
-
p. 4832 - 4836
(2014/07/07)
-
- Synthesis of carbazoles by copper-catalyzed intramolecular C-H/N-H coupling
-
A Cu-catalyzed intramolecular C-H amination for the synthesis of carbazoles has been developed. The key to success is the installation of the picolinamide-based directing group, which is spontaneously removed after the coupling event. The Cu catalysis proceeded smoothly under Pd- and I(III)-free conditions, and its mild oxidation aptitude enables the rapid and concise construction of heteroatom-incorporated carbazole core π-systems.
- Takamatsu, Kazutaka,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
-
p. 2892 - 2895
(2014/06/23)
-
- Reactions of arynes with nitrosoarenes - An approach to substituted carbazoles
-
No transition metals are necessary in the reaction of in situ generated arynes with nitrosoarenes to give substituted carbazoles. Depending on the fluoride source and the solvent, either N-arylated carbazoles or NH-carbazoles are obtained (see scheme; DME=dimethoxyethane, OTf=trifluoromethanesulfonate). In these cascades a C-C and one or two C-N bonds are formed. The reactions are easy to conduct and proceed under mild conditions. Copyright
- Chakrabarty, Shyamal,Chatterjee, Indranil,Tebben, Ludger,Studer, Armido
-
p. 2968 - 2971
(2013/03/29)
-
- Amino-directed RhIII-catalyzed C-H activation leading to one-pot synthesis of N-H carbazoles
-
One-pot synthesis: An efficient amino-directed one-pot synthesis of N-H carbazoles from unprotected 2-aminobiaryl compounds is reported. The free amino unit acts as both a directing group for ortho C-H activation and a functional group for construction of an N-heterocyclic ring (see scheme). Copyright
- Jiang, Qibai,Duan-Mu, Dandan,Zhong, Wei,Chen, Hao,Yan, Hong
-
supporting information
p. 1903 - 1907
(2013/03/28)
-
- A tandem reduction-oxidation protocol for the conversion of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoles via tosylhydrazones through microwave assistance: Efficient synthesis of glycozoline, clausenalene, glycozolicine, and deoxycarbazomycin B and the total synthesis of murrayafoline A
-
A novel and efficient methodology for the synthesis of carbazoles from 1-keto-1,2,3,4-tetrahydrocarbazoles via the corresponding tosylsulfonhydrazones by a one-pot tandem reduction-oxidation protocol using a combination of NaBH4 and Pd-C on MgSO4·7H2O, a solid support, under microwave is developed. The reaction is successfully extended toward the synthesis of several naturally occurring carbazole alkaloids, namely 3-methylcarbazole, glycozoline, clausenalene, glycozolicine, murrayafoline A, and deoxycarbazomycin B, a carbazole derivative that is known to have a promising antimicrobial activity.
- Chakraborty, Suchandra,Chattopadhyay, Gautam,Saha, Chandan
-
-
- Carbocyclization versus oxycyclization on the metal-catalyzed reactions of oxyallenyl C3-linked indoles
-
The preparation of previously unknown (indol-3-yl)-α-allenols and -allenones was accomplished from indole-3-carbaldehydes, through indium-mediated Barbier allenylation reaction taking advantage of the N-(2-pyridyl)sulfonyl group. Metal-catalyzed cyclizations of oxyallenyl C3-linked indoles proceeded in two ways depending on the presence or absence of the N-(2-pyridyl)sulfonyl group. For allenols, gold-catalyzed oxycyclization occurred in the presence of the protecting group; in the absence of the protecting group, palladium- and gold-catalyzed benzannulations operated. On the contrary, under gold catalysis furyl-indoles were obtained as exclusive products from NH-allenones, while 5-endo carbocyclization adducts were the major components starting from N-SO2py-protected allenones. These cyclization reactions have been developed experimentally, and their mechanisms have additionally been investigated by a computational study.
- Alcaide, Benito,Almendros, Pedro,Alonso, Jose M.,Fernandez, Israel
-
p. 6688 - 6701
(2013/07/26)
-
- One-pot synthesis of diarylamines from two aromatic amines via oxidative dearomatization-imino exchange-reductive aromatization
-
A one-pot synthetic strategy for diarylamines using only aromatic amines as starting materials has been developed. This method involved a PhI(OAc) 2-induced oxidative dearomatization of N-sulfonyl protected para-substituted anilines, a Bi(OTf)3-catalyzed imino exchange reaction between N-sulfonyl cyclohexadienimines and aromatic amines, and a CF3COOH/Zn mediated reductive aromatization of the resulting N-aryl cyclohexadienimines.
- Zhang, Li,Wang, Weibin,Fan, Renhua
-
p. 2018 - 2021
(2013/05/23)
-
- Recyclable copper catalyzed nitrogenation of biphenyl halides: A direct approach to carbazoles
-
A novel A21-CuI catalyzed direct nitrogenation of biphenyl halides for the direct synthesis of carbazoles via a direct C-H amination process has been developed. A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C-H amination, which makes this protocol very practical and easy to handle.
- Ou, Yang,Jiao, Ning
-
supporting information
p. 3473 - 3475
(2013/05/22)
-
- One-pot synthesis of carbazoles from cyclohexanones and arylhydrazine hydrochlorides under metal-free conditions
-
One-pot synthesis of carbazoles from cyclohexanones and arylhydrazine hydrochlorides is disclosed. Various substituted carbazoles were obtained in moderate to good yields via a sequence of condensation, cyclization and dehydrogenation under metal free conditions using molecular oxygen as an oxidant.
- Xiao, Fuhong,Liao, Yunfeng,Wu, Mingyue,Deng, Guo-Jun
-
supporting information
p. 3277 - 3280
(2013/01/16)
-
- A series of CBP-derivatives as host materials for blue phosphorescent organic light-emitting diodes
-
We report a series of CBP-derivatives with superior thermal and electronic properties for the use as host materials for blue electrophosphorescent organic light emitting diodes. We applied a systematic variation of the substitution pattern in the 2- and 2′-position of the biphenyl unit and the 3- and 6-position of the carbazole moieties. In contrast to the crystalline parent compound CBP, all methyl and trifluoromethyl substituted derivatives show amorphous behaviour. Substitution in the 2- and 2′-position of the biphenyl causes a twisting of the phenyl rings. Hence, the degree of conjugation of the molecules is limited which leads to enlarged triplet energies of approximately 2.95 eV compared to 2.58 eV for CBP. The methyl substitution at the active 3- and 6-position of the pendant carbazole units yields materials with an electrochemically stable behaviour against oxidation. The Royal Society of Chemistry.
- Schroegel, Pamela,Tomkeviciene, Ausra,Strohriegl, Peter,Hoffmann, Sebastian T.,Koehler, Anna,Lennartz, Christian
-
p. 2266 - 2273
(2011/10/12)
-
- Kinesin spindle protein (KSP) inhibitors with 2,3-fused indole scaffolds
-
Mitotic kinesin spindle protein (KSP) is involved in the assembly of the bipolar spindle during cell division. On the basis of a common 2,3-fused indole substructure within the complex frameworks of terpendole E and other KSP inhibitors, the carbazoles with a bulky alkyl group were identified as a novel KSP inhibitory scaffold. Additionally, among several naturally occurring cell growth inhibitors with 2,3-fused indole structures,β-carboline alkaloids, harman and harmine, showed moderate inhibition of KSP.
- Oishi, Shinya,Watanabe, Toshiaki,Sawada, Jun-Ichi,Asai, Akira,Ohno, Hiroaki,Fujii, Nobutaka
-
experimental part
p. 5054 - 5058
(2010/09/05)
-
- Palladium-catalyzed direct arylation-based domino synthesis of annulated N-heterocycles using alkenyl or (hetero)aryl 1,2-dihalides
-
A palladium-catalyzed reaction sequence consisting of an intermolecular amination and an intramolecular direct arylation enabled highly regioselective syntheses of functionalized indoles or carbazoles and proved to be amenable to the use of inexpensive 1,2dichloroarenes as electrophiles.
- Ackermann, Lutz,Althammer, Andreas,Mayer, Peter
-
scheme or table
p. 3493 - 3503
(2010/02/28)
-
- Rh2(II)-catalyzed synthesis of carbazoles from biaryl azides
-
An array of carbazoles (23 examples) can be synthesized from substituted biaryl azides at 60 °C using substoichio-metric quantities of Rh 2(O2CC3F7)4 or Rh 2(O2CC7H15)4.
- Stokes, Benjamin J.,Jovanovic, Brankica,Dong, Huijun,Richert, Kathleen J.,Riell, Ryan D.,Driver, Tom G.
-
supporting information; experimental part
p. 3225 - 3228
(2009/08/07)
-
- Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: Synthesis and mechanistic study
-
(Chemical Equation Presented) An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.
- Watanabe, Toshiaki,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
-
experimental part
p. 4720 - 4726
(2009/10/02)
-
- DICARBAZOLE AROMATIC AMINE POLYMERS AND ELECTRONIC DEVICES
-
A conjugated or partially conjugated polymer comprising a structural unit of Formula I: I Wherein Ar1 is an aromatic group which contains one or more heteroatoms, or an aromatic group which comprises one or more fused aromatic or non-aromatic rings, said aromatic group may be substituted or unsubstituted; and R1 is alkyl, alkoxy, and aryl group, cyano, or F.
- -
-
-
- Biscarbazol-9-Yl-Substituted Triarylamine-Containing Polymers and Electronic Devices
-
A conjugated or partially conjugated polymer including a structural unit of Formula (I); where T is an aryl or heteroaryl group that may be substituted or unsubstituted, or a C1-C24 alkyl group; R1 is alkyl, alkoxy, aryl group, cyano, or F; and a and b are independently selected from 1, 2 or 3. In addition, a composition of Formula (IV); wherein X is a halogen or a boronate group.
- -
-
-
- One-pot synthesis of carbazole via tandem Suzuki-Miyaura and amination reaction
-
One-pot synthesis of carbazole from two aromatic rings was accomplished by a tandem Suzuki-Miyaura and amination reaction. Our novel phosphine ligand for both reactions efficiently mediates a sequential intermolecular biaryl formation and ring-closing amination. Georg Thieme Verlag Stuttgart.
- Kitamura, Yuki,Yoshikawa, Seiji,Furuta, Takumi,Kan, Toshiyuki
-
p. 377 - 380
(2008/04/01)
-
- Carbazole synthesis by platinum-catalyzed C-H functionalizing reaction using water as reoxidizing reagent
-
Treatment of 1-aminobiphenyl and diphenylamine with catalytic amount of Pt/C in hydrothermal water (250 °C, 4 MPa) affords 9H-carbazole in good yield. In this catalytic cycle, water works as reoxidizing reagent for platinum catalyst. Copyright
- Yamamoto, Mitsuru,Matsubara, Seijiro
-
p. 172 - 173
(2007/10/03)
-
- Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
-
An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps.
- Liu, Zhijian,Larock, Richard C.
-
p. 347 - 355
(2007/10/03)
-
- One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
-
One-pot N-arylation and oxidative coupling can be promoted by a common palladium catalyst in the presence of appropriate additives: palladium-catalyzed N-arylation of anilines with aryl triflates under the standard conditions followed by addition of acetic acid under oxygen or air atmosphere afforded various types of functionalized carbazoles in good to excellent yields. The Royal Society of Chemistry.
- Watanabe, Toshiaki,Ueda, Satoshi,Inuki, Shinsuke,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
-
p. 4516 - 4518
(2008/04/01)
-
- Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes
-
(Chemical Equation Presented) One after the other: A novel palladium-catalyzed domino reaction consisting of an amination and a direct C-H bond arylation allows for a general synthesis of annulated heterocycles starting from readily available 1,2-dichloroarenes and primary as well as secondary anilines (see scheme; Cy = cyclohexyl). This is high-lighted by an efficient synthesis of the natural product murrayafoline A.
- Ackermann, Lutz,Althammer, Andreas
-
p. 1627 - 1629
(2008/02/13)
-
- DBU, a highly efficient reagent for the facile regeneration of (hetero)arylamines from their acetamides and benzamides: Influence of solvent, temperature, and microwave irradiation
-
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) was found to smoothly cleave the N-acetyl and N-benzoyl derivatives of carbazoles, indoles and nitroanilines quickly in refluxing methanol and the parent amines were recovered in excellent yields. Complete cleavage could also be accomplished in acetonitrile solution under reflux and also under microwave irradiation, which, however, required considerably longer periods.
- Chakrabarty, Manas,Ghosh, Nandita,Khasnobis, Shampa,Chakrabarty, Manju
-
p. 265 - 272
(2007/10/03)
-
- Two new carbazole alkaloids from Murraya koenigii
-
Two new alkaloids, 1-formyl-3-methoxy-6-methylcarbazole 1 and 6,7-dimethoxy-1-hydroxy-3-methylcarbazole 2, have been isolated from the leaves of Murraya koenigii. Both the compounds have been identified by spectral as well as chemical evidences, and their structures confirmed by synthesis. Compound 2 is found to be active against Gram-positive and Gram-negative bacteria and fungi.
- Chowdhury,Jha,Bhattacharyya,Mukherjee
-
p. 490 - 494
(2007/10/03)
-
- Synthesis of carbazoles from N-(N,N-diarylamino)phthalimides with aluminum chloride via diarylnitrenium ions
-
Generation of diarylnitrenium ions from N-(N,N-diarylamino)phthalimides by treatment with AlCl3 in benzene or in 1,2-dichloroethane leads to formation of carbazoles by intramolecular C-C bond formation. The reaction proceeds in synthetically useful yields.
- Kikugawa,Aoki,Sakamoto
-
p. 8612 - 8615
(2007/10/03)
-
- Pyridocarbazole derivatives having cGMP-PDE inhibitory activity
-
PCT No. PCT/JP97/01829 Sec. 371 Date Jan. 29, 1998 Sec. 102(e) Date Jan. 29, 1998 PCT Filed May 29, 1997 PCT Pub. No. WO97/45427 PCT Pub. Date Dec. 4, 1997The invention relates to novel pyridocarbazole derivatives having highly selective action in inhibiting cyclic GMP-phosphodiesterase (hereinafter abbreviated as cGMP-PDE), processes for producing such derivatives, agents containing at least one of such derivatives as an active ingredient for preventing and/or treating pulmonary hypertension, ischemic heart diseases or diseases against which the cGMP-PDE inhibitory action is effective, and intermediates useful for the production of pyridocarbazole derivatives.
- -
-
-
- Synthesis of carbazoles from o-cyclohex-2-enylanilines
-
Several carbazoles (4a-f) have been synthesised from o-cyclohex-2- enylanilines by treatment with pyridine hydrotribromide in methylene chloride at 05 °C for 2 h followed by refluxing with Pd-C in diphenyl ether for 1 h.
- Majumdar,Das,Kundu
-
p. 1593 - 1600
(2007/10/03)
-
- New syntheses of murrayafoline-A and murrayaquinone-A via Fischer indolization of 2-sulfonyloxyphenylhydrazone (Fischer indolization and its related compounds. Part 29)
-
Two carbazole alkaloids, murrayafoline-A (4a) and murrayaquinone-A (4b), were synthesized from 1, 2, 3, 4-tetrahydro-8-methanesulfonyloxy-6- methylcarbazole (8) prepared in the application of Fischer indolization of 2- sulfonyloxyphenylhydrazone.
- Murakami, Yasuoki,Yokoo, Hiroshi,Watanabe, Toshiko
-
p. 127 - 132
(2007/10/03)
-
- Molecular rearrangement of sulfur compounds(VII). A pyrolysis of arenesulfonylhydrazine derivatives
-
N-Phenyl-N′-arenesulfonylhydrazine(I-II) on pyrolysis by refluxing in an atmosphere of nitrogen at ca. 240°C give SO2, H2S, NH3, arene, biaryl, aniline, azobenzene, diaryl sulfide, diaryl sulfone, arenesulfonic acid, phenyl hydrazine and carbazole derivatives. N-Benzylidene-N′-benzenesulfonylhydrazone(III) on similar treatment gives the previous products in addition to benzonitrile, bibenzyl, stilbene, 2-phenylindole and 2,3,4,5-tetraphenylthiophene. The observed results have been interpreted in terms of a free radical mechanism involving the homolysis of N - N and S - N bonds.
- Gaber, Abd El-Aal M.,Atalla, Ahmed A.,Kamal El-Dean, Adel M.
-
p. 131 - 136
(2007/10/03)
-
- Microbial transformation of selected carbazole derivatives
-
A strain of Pseudomonas aeruginosa and another of Aspergillus fumigatus are found to have the ability to degrade carbazole derivatives. These strains show different specificities for growth on 1- and 3-methylcarbazoles and accumulate forraylcarbazoles as end products in low yields. Pseudomonas species degrade 1- and 3-formylcarbazoles to the corresponding carboxylic acid derivatives which in turn are decarboxylated to carbazole in high yields. This strain also biotransforms the N-acetylcarbazoles (8, 9 and 10) and the respective deacetyl-derivatives (7,2 and 11) are obtained in good yields. This study provides an evidence in favour of the suggested biotransfonnation of 3-methylcarbazole to carbazole via 3-formylcarbazole and carbazole-3-carboxylic acid in the plants.
- Chakraborty,Chowdhury
-
p. 617 - 620
(2007/10/03)
-