- Synthesis of n-methyl benzenemethane sulfonamide substituted carbazoles and pyrazoles
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Cyclization of 1-(4-hydrazinophenyl)-N-methylmethanesulfonamide hydrochloride (2) with cyclohexanone (3)/N-methyl-4-piperidone (5) afforded the corresponding N-methyl-1-(2,3,4,9-tetrahydro-1H-carbazol-6-yl)methanesulfonamide (4) and N-methyl-1-(2-methyl- 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-8-yl) methane sulfonamide (6). Condensation of compound 2 with substituted aryl β-diketones gave the novel N-methyl-1-[4-(3-methyl-5-phenyl-1H-pyrazol-1- yl)phenyl]methanesulfonamide (8). All the synthesized compounds were characterized by their FT-IR, 1H NMR and mass spectral data.
- Rao, B. Venugopala,Hariharakrishnan,Dubey
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scheme or table
p. 1191 - 1194
(2012/08/07)
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- PREPARATION AND UTILITY OF SUBSTITUTED INDOLES
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Disclosed herein are substituted indoles of Formula I, processes of preparation there of, pharmaceutical compositions thereof, and methods of their use there of.
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Page/Page column 35
(2008/06/13)
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- Piperazine, piperidine and tetrahydropyridine derivatives useful as 5-HT1 recepter agonists
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A class of N-substituted piperazine, piperadine and tetrahyrdopyridine derivatives of formula (I), further substituted at the 4-position by an optionally substituted aryl-alkyl or heteroaryl-alkyl moiety, are selective agonists of 5-HT1 -like r
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- An efficient Fischer indole synthesis of avitriptan, a potent 5-HT(1D) receptor agonist
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An efficient synthesis of antimigraine drug candidate avitriptan (1, BMS 180048) is reported. The key step is a two-phase Fischer indolization reaction between hydrazine 6 and 5-chlorovaler-aldehyde, 20, to give the chloropropylindole 35, which is susceptible to acid-catalyzed degradation under the reaction conditions required for its formation. Sequential coupling of 35 with piperazine, 26, and 4-chloro-5-methoxypyrimidine, 24, gives the title compound in 40-45% overall yield. Significant improvements in the syntheses of the known starting materials, hydrazine 6, 5- chlorovaleraldehyde, 20, and 4-chloro-5-methoxypyrimidine, 24, were also achieved.
- Brodfuehrer,Chen,Sattelberg T.R.,Smith,Reddy,Stark,Quinlan,Reid
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p. 9192 - 9202
(2007/10/03)
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