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Synthesis of 6-substituted pyrido[2,3-b]indoles by electrophilic substitution
Regioselective electrophilic aromatic substitutions, acylation, bromination, and formylation, of unprotected pyrido[2,3-b]indole (α-carbolines) at the C-6 position are described. Alternative conditions for the nitration were investigated, which led to the unexpected appearance of the minor C-8 isomer. Georg Thieme Verlag Stuttgart.
Schneider, Cédric,Gueyrard, David,Popowycz, Florence,Joseph, Beno?t,Goekjian, Peter G.
p. 2237 - 2241
(2007)
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Visible-light-driven Cadogan reaction
Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
supporting information
p. 2582 - 2586
(2021/03/09)

Method for preparing 9H-pyrido[2,3-B]indole
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for preparing 9H-pyrido[2,3-b]indole. Existing preparation methods of the 9H-pyrido[2,3-b]indole are relatively complex in process and relatively low in yield. According to the method for preparing 9H-pyrido[2,3-b]indole in the invention, benzotriazole and 2-bromopyridine are used as raw materials, a substitution reaction of benzotriazole is conducted in a xylene solvent, and then nitrogen removal rearrangement under the action of acid is carried out to obtain the 9H-pyrido[2,3-b]indole. The method is simple in reaction, easy to operate, high in yield, simple in post-treatment, less in wastewater and friendlier to environment.
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Paragraph 0022; 0038; 0041-0042; 0043; 0046-0047; 0048; ...

(2021/08/14)

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)

ORGANIC COMPOUNDS, LIGHE EMITTING DIODE AND LIGHT EMITTING DEVICE HAVING THE COMPOUNDS
The present invention relates to an organic compound having an amine core substituted with three aromatic rings, wherein a part of the three aromatic rings is substituted with a functional group capable of a solution process while the rest of the three aromatic rings is substituted with a hetero-aromatic functional group; and a light-emitting diode and a light-emitting device having the organic compound applied to a light-emitting layer. The organic compound may be used to the light-emitting layer to eliminate the HOMO energy barrier between the light-emitting layer and another light-emitting layer adjacent thereto. Also, the organic compound, when it forms a light-emitting layer in combination with light-emitting particles, may improve interfacial properties between the light-emitting layer and an adjacent layer to improve morphological properties of the light-emitting diode. The organic compound of the present invention, by allowing holes and electrons to be transported and implanted into a light emitting material layer in a balanced manner, may implement light-emitting diodes and light-emitting devices with improved luminance efficiency and capable of low-voltage driving.(110) First electrode(120) Second electrode(AA) Smooth interface morphology ↑COPYRIGHT KIPO 2019
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(2019/08/06)

Compound and application thereof in field of organic light emitting
The invention relates to a compound. The structure of the compound is shown in a following formula (the formula is shown in the description), wherein L1 and L2 are respectively independently selectedfrom single-bond, substituted or unsubstituted arylidene or fused ring sub-aromatic hydrocarbon group containing C6 to C60, and substituted or unsubstituted heteroarylidene or fused heterocyclic sub-aromatic hydrocarbon group containing one or multiple heteroatoms and C5 to C60; Ar1 and Ar2 are respectively independently selected from substituted or unsubstituted arylidene or fused ring aromatic hydrocarbon group containing C6 to C60, and substituted or unsubstituted heteroaryl, arylamine group, secondary amine group or fused heterocyclic aromatic hydrocarbon group containing one or multiple heteroatoms and C5 to C60; at least one of Ar1 and Ar2 is a electron-deficient group. The invention also provides an organic electroluminescence device adopting the novel compound shown in the formula.The organic electroluminescence device has the advantages that the drive voltage is low, and the light emitting efficiency is high.
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(2019/06/08)

Anthraquinone organic electroluminescent material and application thereof
The invention discloses an anthraquinone organic electroluminescent material and application thereof. A general formula compound is shown in a formula (1) in the specification, and in the formula (1),Z is selected from O or S; X1-X8 are independently selected from CR1 or N, wherein R1 is selected from a structure shown in a formula (2) in the specification, or selected from hydrogen, alkyl, arylor heterocyclic aryl, adjacent R1 groups can form a ring, and at least one of R1 groups is selected from the structure (2) shown in the formula (2); in the formula (2), Y1-Y8 are independently selected from CR2 or N, and at least one of the Y1-Y8 is selected from N; R2 is selected from hydrogen, alkyl, aryl or heterocyclic aryl, and adjacent R2 groups can form a ring; L is selected from single bonds, arylidene or heterocyclic arylidene; and when two or more R1 groups are selected from the formula (2), the selected L groups in the formula (2) are not single bonds at the same time. The compoundshows excellent device performance and stability when serving as the light-emitting material in an organic light-emitting device (OLED), and meanwhile the OLED adopting the general formula compound iswithin the scope of right protection.
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Paragraph 0058; 0060; 0067-0068

(2019/11/14)

Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization
An efficient strategy for the intramolecular denitrogenative transannulation/C(sp2)-H amination of 1,2,3,4-tetrazoles bearing C8-substituted arenes, heteroarenes, and alkenes is described. The process involves the generation of the metal-nitrene intermediate from tetrazole by the combination of [CpIrCl2]2 and AgSbF6. It has been shown that the reaction proceeds via an unprecedented electrocyclization process. The method has been successfully applied for the synthesis of a diverse array of α-carbolines and 7-azaindoles.
Das, Sandip Kumar,Roy, Satyajit,Khatua, Hillol,Chattopadhyay, Buddhadeb
p. 8429 - 8433
(2018/07/09)

Organic compound and Organic light emitting diode and organic emitting display device including the same
The present invention provides an organic compound represented by the following chemical formula 1 and having high thermal stability and triplet energy and excellent hole mobility. An organic light emitting diode and an organic light emitting display device in which such organic compound is used for a hole transport layer and/or a P-type charge generation layer have advantages in driving voltage, light emitting efficiency and lifetime.COPYRIGHT KIPO 2018
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(2018/06/15)

Organic electroluminescent material and device
The invention provides an organic compound with a specific structure. The organic compound is characterized by being shown as a general formula (I): the formula (I) is shown in the description; in theformula (I), X1 to X8 are respectively independently selected from CR1 or N respectively, wherein at least one is an N atom; L is a single bond and is C5 to C12 substituted or unsubstituted arylene and heteroarylene; R1 is selected from hydrogen, C1 to C10 aryl or cycloalkyl, C6 to C15 aryl or C6 to C19 condensed ring aryl and at least one is azacarbazole; Ar is substituted or unsubstituted N heterophenyl. The invention discloses an inverse intersystem crossing constant and emission delayed fluorescence rule and the designed compound is used for an organic electroluminescent device, can be used for effectively improving the current efficiency and is an organic electroluminescent material with good performance. The invention also provides the organic electroluminescent device adopting thecompound shown as the general formula.
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(2018/07/28)

ORGANIC ELECTROLUMINESCENT MATERIALS CONTAINING CARBOLINE GROUP AND ORGANIC ELECTROLUMINESCENT DEVICE BY USING THE SAME
An organic electroluminescent material is shown in General Formula (1), wherein R3 is a carboline group, R13 is a carbazole group or a carboline group, R1 to R2, R4 to R12 and R14 to R20 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkyl group, a thioalkyl group, a silyl group and an alkenyl group.
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(2018/04/17)

A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts
A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-α-carboline that is itself readily aromatized to give α-carboline (1).
Yan, Qiao,Gin, Emma,Banwell, Martin G.,Willis, Anthony C.,Carr, Paul D.
p. 4328 - 4335
(2017/04/28)

Discovery of novel dual inhibitors of receptor tyrosine kinases EGFR and IGF-1R
Novel 4-benzylamino benzo-anellated pyrrolo[2,3-b]pyridines have been synthesized with varied substitution patterns both at the molecular scaffold of the benzo-anellated ring and at the 4-benzylamino residue. With a structural similarity to substituted thieno[2,3-d]pyrimidines as epidermal growth factor receptor (EGFR) inhibitors, we characterized the inhibition of EGFR for our novel compounds. As receptor heterodimerization gained certain interest as mechanism of cancer cells to become resistant against novel protein kinase inhibitors, we additionally measured the inhibition of insulin-like growth factor receptor IGF-1R which is a prominent receptor for such heterodimerizations with EGFR. Structure–activity relationships are discussed for both kinase inhibitions depending on the varied substitution patterns. We discovered novel dual inhibitors of both receptor tyrosine kinases with interest for further studies to reduce inhibitor resistance developments in cancer treatment.
Hempel, Cornelius,Totzke, Frank,Sch?chtele, Christoph,Najjar, Abdulkarim,Sippl, Wolfgang,Ritter, Christoph,Hilgeroth, Andreas
p. 271 - 276
(2017/11/10)

ORGANIC ELECTROLUMINESCENT MATERIALS CONTAINING N-PHENYLCARBOLINE AND ORGANIC ELECTROLUMINESCENT DEVICE BY USING THE SAME
An organic electroluminescent material is shown in General Formula (1), wherein one of X1, X2, and X3 is an independent nitrogen atom, and R1 to R14 are each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a thioalkyl group, a silyl group, and an alkenyl group.
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(2017/08/24)

CaMKII INHIBITORS AND USES THEREOF
The present invention provides compounds useful as inhibitors of Ca2+/calmodulin-dependent protein kinase (CaMKII), compositions thereof, and methods of using the same.
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Paragraph 00172-00173

(2016/05/02)

Discovery of dually acting small-molecule inhibitors of cancer-resistance relevant receptor tyrosine kinases EGFR and IGF-1R
Novel benzo-anellated furo- and pyrrolo[2,3-b]pyridines with a 4-benzylamine substitution have been evaluated as inhibitors of the epidermal growth factor receptor (EGFR). Substituent effects on the determined protein kinase affinity have been discussed based on varied benzylamine residues at the differently substituted molecular scaffolds. Docking studies were carried out in order to explore the potential binding modes of the novel inhibitors. The observed activity data encouraged the measurement of the inhibition of the insulin-like growth factor receptor (IGF-1R), which is known to play an important role in the cancer-resistance development against EGFR inhibitors via receptor heterodimerizations with IGF-1R. We identified novel dual inhibitors of both kinases and report their first cancer cell growth inhibition data.
Hempel, Cornelius,Najjar, Abdulkarim,Totzke, Frank,Sch?chtele, Christoph,Sippl, Wolfgang,Ritter, Christoph,Hilgeroth, Andreas
supporting information
p. 2159 - 2166
(2016/11/17)

Organic electroluminescent materials and devices
Novel phosphorescent platinum complexes containing tetradentate ligands are provided. The disclosed compounds have three 6-membered metallocycle units in each tertadentate ligand. The disclosed compounds have desirable electronic properties that make them useful when incorporated into a variety of OLED devices.
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Page/Page column 196-197

(2016/10/27)

Synthesis of α-carboline
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He, Linli,Allwein, Shawn P.,Dugan, Benjamin J.,Knouse, Kyle W.,Ott, Gregory R.,Zificsak, Craig A.
p. 272 - 285
(2017/02/23)

HOST COMPOUNDS AND ORGANIC LIGHT EMITTING DIODE DEVICES COMPRISING THE SAME
A host compound according to an embodiment of the present invention is characterized by being presented by chemical formula 1. Here, R_1 and R_2 is independently anyone selected among hydrogen, heavy hydrogen, an alkyl group of C1 to C20, an aromatic ring compound, and a hetero ring compound.COPYRIGHT KIPO 2015
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(2016/10/20)

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device adopting the same, and more specifically, to an organic electroluminescent compound represented by chemical formula 1 below. In the chemical formula 1, ring A and ring B are independently a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a five- or six-membered heteroaromatic ring fused with an aromatic ring, or a monocyclic or polycyclic aromatic ring fused with a five- or six-membered heteroaromatic ring, where the ring A and ring B cannot both be a monocyclic aromatic ring. The organic electroluminescent compound according to the present invention shows good luminous efficiency, and superior material color purity and lifetime characteristics, thereby enabling manufacture of an OLED device with excellent driving time.COPYRIGHT KIPO 2016
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Paragraph 0121-0123

(2016/10/10)

COMPOUNDS AND METHODS FOR TREATING CANCERS
Provided are carbazole and carbazole-like compounds (e.g., pyridoindole and pyrrolodipyridine) compounds, that can be used to selectively kill cancer cells, specifically androgen-receptor expressing prostate cancer cells. Also provided is a method of treating AR-positive prostate cancer in a subject diagnosed with or suspected of having AR positive or negative cancer, comprising administering an effective amount of a carbazole and carbazole-like compound to said subject.
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Paragraph 0126; 0127

(2014/10/04)

HETEROCYCLIC COMPOUNDS AS INHIBITORS OF FATTY ACID BIOSYSNTHESIS FOR BACTERIAL INFECTIONS
The present invention relates to novel heterocyclic compounds which specifically inhibit bacterial FabI and can be used for the treatment of Staphylococcal infections.
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Paragraph 0076; 0077

(2014/09/16)

Discovery of 4-anilino α-carbolines as novel Brk inhibitors
Dysregulation of cell signalling processes caused by an enhanced activity of protein kinases mainly contributes to cancer progression. Protein kinase inhibitors have been established as promising drugs that inhibit such overactive protein kinases in cancer cells. The formation of metastases, which makes a therapy difficult, remains a great challenge for cancer treatment. Recently, breast tumor kinase (Brk) was discovered as novel and interesting target for a cancer therapy because Brk participates in both cell dysregulation and metastasis. We discovered 4-anilino substituted α-carboline compounds as a novel class of highly active Brk inhibitors. In the current work, structure-activity relationships are discussed including docking results obtained for 4-anilino α-carbolines. A first profiling of selective kinase inhibition and a proof of concept for the antiproliferative effects is demonstrated. These results qualify the compounds as a promising class of novel antitumor agents.
Mahmoud, Kazem Ahmed,Krug, Martin,Wersig, Tom,Slynko, Inna,Sch?chtele, Christoph,Totzke, Frank,Sippl, Wolfgang,Hilgeroth, Andreas
p. 1948 - 1951
(2014/04/17)

Novel inhibitors of breast cancer relevant kinases Brk and HER2
Novel 4-anilino pyrido[2,3-b]indoles have been discovered as inhibitors of the breast cancer relevant protein kinase Brk. Within this first series favourable aniline substituents have been characterized. Combinations with substituents of the molecular scaffold have been further investigated and led to additional nanomolar Brk inhibitors. Due to the reported role of Brk in breast cancer progression via HER2 activation we determined the inhibition profile of our novel Brk inhibitors to additionally inhibit HER2. These studies characterized the first dually acting Brk and HER2 inhibitor and the first exclusive HER2 inhibitors. This journal is the Partner Organisations 2014.
Mahmoud, Kazem Ahmed,Wersig, Tom,Slynko, Inna,Totzke, Frank,Sch?chtele, Christoph,Oelze, Markus,Sippl, Wolfgang,Ritter, Christoph,Hilgeroth, Andreas
supporting information
p. 659 - 664
(2014/05/06)

CaMKII INHIBITORS AND USES THEREOF
The present invention provides compounds useful as inhibitors of Ca2+/calmodulindependent protein kinase (CaMKII), compositions thereof, and methods of using the same. Cardiovascular disease remains the number one cause of death in developed countries. Furthermore, incidence of cardiovascular disease has increased dramatically in developing countries. Although cardiovascular disease usually affects older adults, the antecedents of cardiovascular disease, notably atherosclerosis, begin in early life, making primary prevention efforts necessary from childhood.
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Paragraph 00157-00158

(2014/09/29)

HETEROCYCLIC COMPOUNDS AS INHIBITORS OF FATTY ACID BIOSYNTHESIS FOR BACTERIAL INFECTIONS
The present invention relates to novel heterocyclic compounds which specifically inhibit bacterial Fab I and can be used for the treatment of Staphylococcal infections.
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Page/Page column 18-19

(2013/04/10)

Effect of the position of nitrogen in pyridoindole on photophysical properties and device performances of α-, β-, γ-carboline based high triplet energy host materials for deep blue devices
Three carboline derivatives with nitrogen at different positions of the pyridoindole unit were synthesized and the effect of the position of nitrogen on the photophysical properties and device performances was investigated. β-Carboline was effective in obtaining high triplet energy and stabilizing energy levels, while α-carboline was better than other carbolines in terms of quantum efficiency. However, γ-carboline could not stabilize the LUMO level and low quantum efficiency was obtained.
Im, Yirang,Lee, Jun Yeob
p. 5948 - 5950
(2013/07/19)

A new route to α-carbolines based on 6π-electrocyclization of indole-3-alkenyl oximes
Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 C under microwave irradiation undergo loss of the Boc-group, and 6π-electrocyclization to α-carbolines, following aromatization by loss of methanol (11 examples, 30-90% yield).
Markey, Sophie J.,Lewis, William,Moody, Christopher J.
p. 6306 - 6308
(2014/01/17)

SUBSTITUTED OLIGOAZACARBAZOLES FOR LIGHT EMITTING DIODES
Novel compounds containing substituted oligoazacarbazole chains are provided. Y- X-Z, wherein Y is selected from the group consisting of: A- B -C-D- A -B-C- A-B- wherein A, B, C, and D are independently selected from the compound of formula (I) wherein X is an aryl or heteroaryl linker that is optiorially further substituted; wherein Y and X are connected through a C—N bond; and wherein Z is selected from the group consisting of dibenzothiphene, dibenzofuran, dibenzoselenophene, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene that is optionally further substituted. These compounds are useful in organic light emitting devices, in particular as hosts in the emissive layer of such devices.
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Page/Page column 52-53

(2012/11/07)

SUBSTITUTED OLIGOAZACARBAZOLES FOR LIGHT EMITTING DIODES
Novel compounds containing substituted oligoazacarbazole chains are provided. These compounds are useful in organic light emitting devices, in particular as hosts in the emissive layer of such devices.
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(2012/10/18)

Synthesis of carbolines by photostimulated cyclization of anilinohalopyridines
A general synthetic route to prepare all four carboline regioisomers by photostimulated cyclization of anilinohalopyridines is described. The methodology affords various substituted carbolines in good to excellent yields. In the case of α-carbolines, the SRN1 methodology complements previously reported palladium-catalyzed cyclization approaches.
Laha, Joydev K.,Barolo, Silvia M.,Rossi, Roberto A.,Cuny, Gregory D.
experimental part
p. 6421 - 6425
(2011/09/15)

One-pot synthesis of α-carbolines via sequential palladium-catalyzed aryl amination and intramolecular arylation
A one-pot synthesis of α-carbolines via a palladium-catalyzed aryl amination followed by intramolecular arylation is described. 2,3-Dichloro- and 2,3-dibromopyridines have been shown to react with readily available anilines to obtain various substituted α-carbolines in moderate to excellent yields.
Laha, Joydev K.,Petrou, Philip,Cuny, Gregory D.
supporting information; experimental part
p. 3152 - 3155
(2009/08/07)

γ-Carboline derivatives with anti-bovine viral diarrhea virus (BVDV) activity
Based on anti-viral screening of our heteroaromatics derived from thalidomide, the γ-carboline skeleton has been identified as a superior scaffold structure for compounds with potent anti-bovine viral diarrhea virus (BVDV) activity. Structural development studies led to a potent anti-viral agent, SK5M (5-methyl-γ-carboline), with the EC50 of 0.26 μM.
Sako, Kumiko,Aoyama, Hiroshi,Sato, Shinichi,Hashimoto, Yuichi,Baba, Masanori
p. 3780 - 3790
(2008/12/20)

Synthesis of α-carbolines starting from 2,3-dichloropyridines and substituted anilines
9H-α-Carbolines have been prepared via consecutive intermolecular Buchwald-Hartwig reaction and Pd-catalyzed intramolecular direct arylation from commercially available 2,3-dichloropyridines and substituted anilines. The combination of a high reaction temperature (180°C) and the use of DBU were found to be crucial for the intramolecular direct arylation reactions of the 3-chloro-N-phenylpyridin-2-amines as no reaction was observed at 120°C and 180°C using different inorganic and other organic bases. On the other hand, nitrogen-methylated pyridine analogues of these substrates {N-[3-chloro-1- methylpyridin-2(1H)-ylidene]anilines} do undergo ring closure at 120°C, with K3PO4 as base, affording the respective 1-methyl-1H-α-carbolines in good yields.
Hostyn, Steven,Van Baelen, Gitte,Lemiere, Guy L. F.,Maes, Bert U. W.
supporting information; experimental part
p. 2653 - 2660
(2009/08/14)

ALPHA-CARBOLINES AS CDK-1 INHIBITORS
The present invention embraces compounds of the general formula (I) in which R2 to R5 and X are as defined in Claim 1, these compounds being suitable for treating diseases characterized by excessive or abnormal cell proliferation, and also embraces their use for producing a medicinal product having the aforementioned properties.
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Page/Page column 109

(2010/11/25)

An improved synthesis of α-carbolines under microwave irradiation
α-Carbolines are interesting core structures for designing DNA-interacting small molecules. However, these compounds are not commercially available and their synthetic methods are low yielding or time consuming. The shortest synthetic route, the modified Graebe-Ullmann reaction, has been optimized by using microwave heating in four different types of apparatus to give shorter reaction times and enhanced yields. Optimized conditions enabled the preparation of a small library of α-carbolines.
Vera-Luque, Patricia,Alajarin, Ramon,Alvarez-Builla, Julio,Vaquero, Juan J.
p. 415 - 418
(2007/10/03)

Catalytic C-H Functionalization Driven by CO as a Stoichiometric Reductant: Application to Carbazole Synthesis
(Equation presented) A palladium-catalyzed regioselective C-H bond functionalization driven by CO as the stoichiometric reductant is described. Nitrogen heterocycles, e.g., carbazoles, are accessible in good to excellent yields with use of palladium acetate and 70 psig of carbon monoxide at 140°C.
Smitrovich, Jacqueline H.,Davies, Ian W.
p. 533 - 535
(2007/10/03)

A new deprotection procedure for the n-methoxymethyl group of n-methoxymethyl-heterocyclic compounds
A new deprotection procedure regarding the N-methoxymethyl (MOM) group was revealed during the total synthesis of oxopropalines D and G. We describe the deprotection method of N-MOM-heterocyclic compounds and its utilization.
Kuwada, Takeshi,Fukui, Miyako,Hirayama, Maho,Nobuhiro, Junko,Choshi, Tominari,Hibino, Satoshi
p. 325 - 332
(2007/10/03)

Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction
Four parent carbolines and the corresponding 5- or 9-methylsulfonyl derivatives were synthesized by the palladium-catalyzed intramolecular arylation reaction of ortho-bromo-substituted anilinopyridines which were prepared by the palladium-catalyzed amination reaction of iodobenzenes with aminopyridines. Carbazole and its 9-methylsulfonyl derivative were also synthesized by the same method.
Iwaki, Takehiko,Yasuhara, Akito,Sakamoto, Takao
p. 1505 - 1510
(2007/10/03)

Effect of methanesulfonyl group on the regioselectivity of photocyclization of arylheterylamine derivatives
Irradiation of arylheterylamines with a methanesulfonyl leaving group ortho to the amino group produces nonselective cyclization to form either a C-C (arylpyridylamines) or a C-N (arylpyrimidylamines) bond. When the methanesulfonyl group is a substituent and chlorine is a leaving group, regioselective photocyclization is observed with C-N bond formation. New pyrido- and pyrimido[1,2-a]benzimidazole derivatives with a methanesulfonyl group in the benzene ring, as well as pyrimido[1,2-a]perimidine derivatives are described. The different regioselectivity of photocyclization of these classess of compounds is explained in terms of radical-cation and electrocyclic reaction mechanisms.
Frolov
p. 1254 - 1261
(2007/10/03)

Pyrolysis of 1-substituted pyrazoles and chloroform at 550°C: Formation of α-carboline from 1-benzylpyrazoles
Pyrolysis of 13CH3 labelled 1-methylpyrazole 8 with chloroform at 550°C in a continuous flow reactor yields unlabelled 2-chloropyrimidine 9 and 2-cyanopyrrole 10 labelled at the cyano group. However, pyrolysis of 1-benzylpyrazole 14 with chloroform under similar conditions gives 9,2-phenylpyrimidine 13 and, as the major product, α-carboline 15. Pyrolysis of several substituted 1-(arylmethyl)pyrazoles and the use of 13C and 15N labelled compounds provides direct evidence by which the positions of 7 atoms of 1-benzylpyrazole can be located in the α-carboline. These data support the mechanisms suggested for the formation of 9, 10, and 15.
Bhatti, Inayat A.,Busby, Reginald E.,Bin Mohamed, Murtedza,Parrick, John,Shaw, C. J. Granville
p. 3581 - 3585
(2007/10/03)

Effect of pressure on processes modelling the Maillard reaction
The Maillard reaction between tryptophan and glucose or xylose was studied as a function of pressure. Using model reactions, volumes of activation for the formation of the intermediate imine and the Amadori rearrangement and for the decomposition of the aminoketose were measured as -14, 8 and 17 cm3mol-1, respectively. Pressure therefore accelerates the initial reactions but retards the formation of the final heterocyclic products and melanoidins. Oxygen was found to accelerate the latter reaction.
Isaacs, Neil S.,Coulson, Mark
p. 639 - 644
(2007/10/03)

Connection between metalation and cross-coupling strategies. A new convergent route to azacarbazoles
New convergent synthesis of azacarbazoles through metalation, cross-coupling reaction and intramolecular substitution via (2-aminobenzene)boronic acid and ortho-fluoroiodopyridines.
Rocca, Patrick,Marsais, Francis,Godard, Alain,Queguiner, Guy
p. 49 - 64
(2007/10/02)

DECOMPOSITION OF 3-(4-TRIFLUOROMETHYLPHENYL)1,2,3-TRIAZOLOPYRIDINE
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Kaczmarek, Lukasz,Nantka-Namirski, Pawel
p. 1021 - 1025
(2007/10/02)

Mass spectrometric study of α-carbolines
A series of α-carbolines were subjected to mass-spectrometric analysis. It is shown that these compounds are extremely stable with respect to electron impact. From 40 to 60% of the total ion current goes into the production of molecular ions during dissociative ionization. The mass spectra of these compounds are simple: the maximum peak corresponds to the molecular peak in the spectrum. The formation of the [M-1]+ ion and the detachment of a methyl group in monomethylcarbolines ([M-15]) are determined by the position of the methyl group. The mass-spectral fragmentation confirms the proposed scheme for the formation of α-carbolines from arylhydrazones and δ6-keto nitriles. A method for the synthesis of α-carbolines on the basis of accessible arylsulfamidoindoles is proposed.
Sharbatyan,Kost,Men'shikov,Yudin,Chernyshova
p. 926 - 932
(2007/10/02)

TRIAZOLOPYRIMIDINES. VII. THE PHOTOCHEMICAL TRANSFORMATION OF 3-PHENYL-3H-1,2,3-TRIAZOLOPYRIMIDINES INTO 9H-PYRIMIDOINDOLES
The photolysis of 3-phenyl-3H-1,2,3-triazolopyrimidines in dioxane, benzene and methanol gave 9H-pyrimidoindoles in moderate yields.Similarly, 3-phenyl-3H-1,2,3-triazolopyridines were easily transformed by the photolysis into 9H-pyridoindoles.
Higashino, Takeo,Hayashi, Eisaku,Matsuda, Hideaki,Katori, Tatsuhiko
p. 483 - 487
(2007/10/02)