- One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles
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A one-pot Barluenga coupling between N-tosylhydrazones and nitro-benzyl bromide, followed by deoxygenation of ortho-nitrostyrenes, and subsequent cyclization has been developed, providing a new way to synthesize various C2-arylindoles. This method exhibits a good substrate scope and functional group tolerance, and it allows an access to NH-free indoles, which can present a potential utility in medicinal chemistry applications.
- Bzeih, Tourin,Zhang, Kena,Khalaf, Ali,Hachem, Ali,Alami, Mouad,Hamze, Abdallah
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p. 228 - 238
(2019/01/04)
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- Ring-Opening of Indoles: An Unconventional Route for the Transformation of Indoles to 1 H-Pyrazoles Using Lewis Acid
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An unusual transformation of indoles to pyrazoles via an aromatic ring-opening strategy has been developed. The salient feature of this strategy involves the C2-N1 bond opening and concomitant cyclization reaction of the C2=C3 bond of the indole moiety with the tosylhydrazone, which proceeds under transition-metal and ligand free conditions. This ring-opening functionalization of indoles provides a wide scope of differently substituted pyrazoles.
- Panda, Subhankar,Pradhan, Nirmalya,Manna, Debasis
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supporting information
p. 573 - 578
(2018/09/25)
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- Synthesis and activity of substituted heteroaromatics as positive allosteric modulators for α4β2α5 nicotinic acetylcholine receptors
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The design and synthesis of a series of substituted heteroaromatic α4β2α5 positive allosteric modulators is reported. The optimization and development of the heteroaromatic series was carried out from NS9283, and several potent analogues, such as 3-(5-(py
- Jin, Zhuang,Khan, Pasha,Shin, Youseung,Wang, Jingyi,Lin, Li,Cameron, Michael D.,Lindstrom, Jon M.,Kenny, Paul J.,Kamenecka, Theodore M.
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p. 674 - 678
(2014/01/23)
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- Microwave assisted efficient aminocarbonylation of N-tosylhydrazones with molybdenum hexacarbonyl and amines
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An efficient aminocarbonylation of N-tosylhydrazones derived from aromatic aldehydes and ketones mediated by molybdenum hexacarbonyl is reported. This method is palladium-free and provides a rapid access to the α-aryl acetamides in moderate to good yields.
- Rao, K. Penta,Basak, Ashok K.,Raju, Amancha,Patil, Vikas S.,Reddy, L. Krishnakanth
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supporting information
p. 5510 - 5513
(2013/09/23)
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- Synthesis of substituted 1 H-indazoles from arynes and hydrazones
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The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.
- Li, Pan,Wu, Chunrui,Zhao, Jingjing,Rogness, Donald C.,Shi, Feng
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experimental part
p. 3149 - 3158
(2012/07/14)
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- Reductive azidation of carbonyl compounds via tosylhydrazone intermediates using sodium azide
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Simple and direct: Aldehydes and ketones can be transformed into alkyl azides through a reductive coupling of the corresponding tosylhydrazones in a process that takes place simply in the presence of K2CO3, tetrabutylammonium bromide
- Barluenga, Jose,Tomas-Gamasa, Maria,Valdes, Carlos
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supporting information; experimental part
p. 5950 - 5952
(2012/07/03)
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- TETRAZOLE DERIVATIVES AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS
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This invention relates to novel tetrazole derivatives, which are found to be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.
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Page/Page column 18
(2011/07/07)
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- TETRAZOLE DERIVATIVES AS NICOTINIC ACETYLCHOLINE RECEPTOR MOUDLATORS
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This invention relates to novel tetrazole derivatives, which are found to be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders
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Page/Page column 18-19
(2011/07/07)
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- Synthesis of 3-substituted indazoles from arynes and N-tosylhydrazones
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Readily available, stable, and inexpensive N-tosylhydrazones react with arynes under mild reaction conditions to afford 3-substituted indazoles in moderate to good yields. The reaction appears to involve a dipolar cycloaddition of in situ generated diazo
- Li, Pan,Zhao, Jingjing,Wu, Chunrui,Larock, Richard C.,Shi, Feng
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supporting information; experimental part
p. 3340 - 3343
(2011/09/12)
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- 2, 5-DISUBSTITUTED TETRAZOLE DERIVATIVES AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS
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This invention relates to novel tetrazole derivatives of formula (I), which are found to be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro- degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.
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Page/Page column 17-18
(2010/10/03)
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- NEW CHEMICAL COMPOUNDS
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The present invention encompasses compounds of general formula (1) wherein the groups R2 to R4, L, Q and n are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use for preparing a pharmaceutical composition with the above-mentioned properties.
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Page/Page column 57
(2009/03/07)
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- One-pot transformation of nitriles into aldehyde tosylhydrazones
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Reduction of various nitriles with Raney nickel and sodium hypophosphite in aqueous acetic acid and pyridine in the presence of tosylhydrazine gave the corresponding aldehyde tosylhydrazones in good yield.
- Tóth, Marietta,Somsák, László
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p. 2723 - 2725
(2007/10/03)
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- Cyclising Nucleophilic Addition to Azinium Systems. Part 2. Reactions of 3-Acylpyridinium Hydrazones.
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3-Acyl-1-methylpyridinium tosyl- and benzoylhydrazines lose a side-chain N-hydrogen on treatment with mild base thus forming zwitterions, isolable in some cases; intramolecular nucleophilic cyclising addition to the pyridinium nucleus in these was observe
- Street, Jonathan D.,Baradarani, M. Mehdi,Beddoes, Roy L.,Mills, Owen S.,Joule, John A.
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p. 1247 - 1285
(2007/10/02)
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- Antineoplastic and biochemical properties of arylsulfonylhydrazones of 2 formylpyridine N oxide
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The structural parameters necessary for the antineoplastic potency of a new class of anticancer agents, arylsulfonylhydrazones of 2 formylpyridine N oxide, were examined in mice bearing Sarcoma 180 ascites cells. The findings indicated that (a) replacement of the pyridine ring with benzene quinoline, or isoquinoline resulted in loss of activity, (b) movement of the formylhydrazone side chain from the 2 to the 3 or 4 positions of the pyridine N oxide produced inactive agents, (c) the pyridine N oxide function was essential for anticancer activity, except for 4 substituted derivatives which were active without the N oxide group, (d) replacement of the SO2 group by CO resulted in complete loss of activity, and (e) a carbon atom could be inserted between the SO2 and aryl ring with retention of anticancer potency. One of the most active members of this series, 1 oxidopyridine 2 carboxaldehyde p toluenesulfonylhydrazone exhibited antineoplastic, activity against a broad spectrum of transplanted tumors including Sarcoma 180, Hepatoma 129, Ehrlich carcinoma, leukemia L1210, and a subline of Sarcoma 180 resistant to α (N) heterocyclic carboxaldehyde thiosemicarbazones. This agent caused inhibition of thymidine 3H and uridine 3H incorporation into DNA and RNA respectively, of Sarcoma 180 ascites cells; protein biosynthesis was relatively insensitive to the action of this compound.
- Sartorelli,Agrawal,Booth,Pittman,Bartholomew
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p. 830 - 833
(2007/10/05)
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