- Novel one-pot synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via copper-free Sonogashira coupling reaction
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Abstract: A novel, simple, and efficient protocol is described for the synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via the one-pot reaction of phenol or 2-naphthol derivatives, propargyl bromide, and N-alkyl-3-chloroquinoxaline-2-amines in the presence of palladium catalyst. This one-pot reaction is carried out in the absence of any copper salt at room temperature. The reaction product is dependent on the nature of the base used. The use of morpholine, as the base, affords the final cyclized product, and triethylamine only gives the coupling product. Graphical abstract: [Figure not available: see fulltext.].
- Keivanloo, Ali,Fakharian, Mahsa,Nabid, Mohammad Reza,Amin, Amir Hossein
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p. 151 - 160
(2019/03/12)
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- Nucleophilic aromatic substitution of heterocycles using a high-temperature and high-pressure flow reactor
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We report herein a high-temperature and high-pressure continuous-flow protocol to carry out nucleophilic aromatic substitution (SNAr) of heterocycles with nitrogen nucleophiles. Utilizing the Phoenix Flow Reactor in parallel with Design-of-Experiment software enabled rapid optimization of the SNAr protocol. This protocol facilitated efficient synthesis of a broad range of 2-aminoquinazolines, and was extended to 2-aminoquinoxalines and 2-aminobenzimidazoles.
- Charaschanya, Manwika,Bogdan, Andrew R.,Wang, Ying,Djuric, Stevan W.
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p. 1035 - 1039
(2016/02/18)
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