Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-methyl-3,5-dinitrobenzaldehyde and closely related substrates. Acetic acid serves as the solvent and sole promoter of these transformations which involve dual C-H functionalization.
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http://dx.doi.org/10.1021/acs.orglett.9b00438 | DOI Listing |
Org Lett
February 2020
Center for Heterocyclic Compounds, Department of Chemistry , University of Florida, Gainesville , Florida 32611 , United States.
Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with -cyanomethylbenzaldehydes. These amine α-C-H bond functionalization reactions are promoted by acetic acid. The resulting β-aminonitriles can be converted to the corresponding β-aminoalcohols in diastereoselective fashion.
View Article and Find Full Text PDFOrg Lett
March 2019
Center for Heterocyclic Compounds, Department of Chemistry , University of Florida, Gainesville , Florida 32611 , United States.
Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-methyl-3,5-dinitrobenzaldehyde and closely related substrates. Acetic acid serves as the solvent and sole promoter of these transformations which involve dual C-H functionalization.
View Article and Find Full Text PDFOrg Lett
July 2018
Center for Heterocyclic Compounds, Department of Chemistry , University of Florida, Gainesville , Florida 32611 , United States.
Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-(2-oxoethyl)malonates in the presence of catalytic amounts of benzoic acid. These reactions install a fully saturated five-membered ring and provide access to structures closely related to the natural products crispine A and harmicine.
View Article and Find Full Text PDFOrg Lett
December 2017
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.
α-Ketoamides undergo redox-annulations with cyclic secondary amines, such as 1,2,3,4-tetrahydroisoquinoline, pyrrolidine, piperidine, and morpholine. Catalytic amounts of benzoic acid significantly accelerate these transformations. This approach provides polycyclic imidazolidinone derivatives in typically good yields.
View Article and Find Full Text PDFChemistry
September 2015
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854 (USA) http://seidel-group.com.
Cyclic amines such as pyrrolidine undergo redox-annulations with 2-formylaryl malonates. Concurrent oxidative amine α-CH bond functionalization and reductive N-alkylation render this transformation redox-neutral. This redox-Mannich process provides regioisomers of classic Reinhoudt reaction products as an entry to the tetrahydroprotoberberine core, enabling the synthesis of (±)-thalictricavine and its epimer.
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