- Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties
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A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.
- Hernández-Ruiz, Raquel,Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Fernández-Rodríguez, Manuel A.,Tapia, M. José,Sanz, Roberto
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supporting information
p. 13613 - 13623
(2021/08/23)
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- Gold(I)/chiral br??nsted acid catalyzed enantioselective hydroamination-hydroarylation of alkynes: The effect of a remote hydroxyl group on the reactivity and enantioselectivity
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The catalytic enantioselective hydroamination-hydroarylation of alkynes under the catalysis of (R3P)AuMe/(S)-3,3a?2-bis(2,4,6-triisopropylphenyl)-1,1a?2-bi-naphthyl-2,2a?2-diyl hydrogenphosphate ((S)-TRIP) is reported. The alkyne was reacted with a range of pyrrole-based aromatic amines to give pyrrole-embedded aza-heterocyclic scaffolds bearing a quaternary carbon center. The presence of a hydroxyl group in the alkyne tether turned out to be very crucial for obtaining products in high yields and enantioselectivities. The mechanism of enantioinduction was established by carefully performing experimental and computational studies.
- Shinde, Valmik S.,Mane, Manoj V.,Vanka, Kumar,Mallick, Arijit,Patil, Nitin T.
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p. 975 - 979
(2015/02/05)
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- Synthesis of pyrrolnitrin and related halogenated phenylpyrroles
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A general approach to halogenated arylpyrroles, including the antifungal natural product pyrrolnitrin, is described using newly synthesized halogenated pyrroles and 2,6-disubstituted nitrobenzenes or 2,6-disubstituted anilines.
- Morrison, Matthew D.,Hanthorn, Jason J.,Pratt, Derek A.
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supporting information; experimental part
p. 1051 - 1054
(2009/07/18)
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- Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy
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(Chemical Equation Presented) Iterative and regioselective metal-catalyzed C-H bondfunctionalization has been utilizedto develop a strategy for the first total synthesis of the pyrrole alkaloid rhazinicine (see scheme).
- Beck, Elizabeth M.,Hatley, Richard,Gaunt, Matthew J.
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p. 3004 - 3007
(2008/12/23)
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