- Electrochemical synthesis of 1,2,4-triazole-fused heterocycles
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A reagent-free intramolecular dehydrogenative C-N cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free protocol which can be carried out on a gram scale easily. This novel method was applied to the synthesis of one of the top-selling drugs Xanax and late stage functionalization for generating chemical diversity in biologically relevant lead molecules.
- Ye, Zenghui,Ding, Mingruo,Wu, Yanqi,Li, Yong,Hua, Wenkai,Zhang, Fengzhi
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p. 1732 - 1737
(2018/04/30)
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- 1-Halomethyl-6-phenyl-4H-s-[4,3-a][1,4]benzodiazepines
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1-Substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula II: STR1 wherein R0 is selected from the group consisting of hydrogen, methyl, ethyl, fluorine, chlorine, and bromine, and X is selected from fluorine, chlorine, and bromine; wherein R1 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms inclusive; wherein R2, R3, R4, and R5 are selected from the group consisting of hydrogen, alkyl, as defined above, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, and alkylsulfonyl, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are prepared by reacting a compound of the formula: STR2 wherein R1, R2, R3 R4, and R5 are defined as above, with an haloacyl chloride or haloacyl bromide of the formula STR3 wherein Ro and X are defined as above and X' is chlorine or bromine. The new products of formula II including their pharmacologically acceptable acid addition salts are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds, and if X=X"=Cl or Br they are useful as intermediates for cyano, alkylthio and dialkylamino products of high sedative and tranquilizing activity.
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- Benzodiazepine derivatives
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Benzodiazepine derivatives of the general formula STR1 where R1 is hydrogen or a hydrocarbon residue of 1-8 carbon atoms, R2 is hydrogen or lower alkyl and rings A and B are unsubstituted or substituted by nitro, trifluoromethyl, halogen, lower alkyl or lower alkoxy, the nitrogen atom in the 5-position being unsubstituted or substituted by an oxygen atom, useful as muscle relaxants, anticonvulsants, sedatives and tranquilizing agents, and processes for production thereof. Also provided are novel intermediates of the general formula STR2 where R2 has the above meaning, rings A and B are unsubstituted or substituted as above and the nitrogen atom in the 4-position is unsubstituted or substituted by an oxygen atom.
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