Reactions that require strictly dry conditions are challenging to translate to a DNA-encoded library format. Controlled pore glass solid support-connected DNA oligonucleotide-aldehyde conjugates could be condensed with SnAP reagents and cyclized to various sp-rich heterocycles. The Boc-group of products provided a handle for product purification, and its facile removal under acidic conditions was tolerated by a chemically stabilized barcode. The reaction provides reagent-based scaffold diversity with functionalities for further library synthesis.
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http://dx.doi.org/10.1021/acs.orglett.2c00228 | DOI Listing |
Org Biomol Chem
April 2024
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China.
An efficient, diversity-oriented synthesis of indole-1,2-fused 1,4-benzodiazepines, tetrahydro-β-carbolines, and 2,2'-bis(indolyl)methanes was established starting from tosyl-protected tryptamine. These diverse privileged skeletons were controllably constructed by adjusting different hydride donors and Brønsted acids. A variety of indole-1,2-fused 1,4-benzodiazepines were facilely accessed using benzaldehydes bearing cyclic amines as hydride donors a cascade -alkylation/dehydration/[1,5]-hydride transfer/Friedel-Crafts alkylation sequence.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
June 2023
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.
A single-handed poly(quinoxaline-2,3-diyl) (PQX) has been found to serve as a new type of chiral shift reagent (CSR) for determining the enantiomeric ratio by NMR spectroscopy. Even though there is no specific binding site in the PQX, its nonbonding interaction with chiral analytes leads to a significant shift of the NMR chemical shift, allowing quantification of the enantiomeric ratio. The new type of CSR has the advantages of a wide scope of analytes including ethers, haloalkanes, and alkanes, easy tunability of the degree of chemical shifts by measurement temperature, and erasability of proton signals of CSR because of the short spin-spin (T ) relaxation of the macromolecular scaffold.
View Article and Find Full Text PDFOrg Lett
February 2022
TU Dortmund University, Faculty of Chemistry and Chemical Biology, Medicinal Chemistry, Otto-Hahn-Str. 6, 44227 Dortmund, Germany.
Reactions that require strictly dry conditions are challenging to translate to a DNA-encoded library format. Controlled pore glass solid support-connected DNA oligonucleotide-aldehyde conjugates could be condensed with SnAP reagents and cyclized to various sp-rich heterocycles. The Boc-group of products provided a handle for product purification, and its facile removal under acidic conditions was tolerated by a chemically stabilized barcode.
View Article and Find Full Text PDFBioorg Chem
January 2022
Department of Chemistry, Faculty of Arts and Sciences, Marmara University, 34722 Istanbul, Turkey.
Monoamine oxidase (EC 1.4.3.
View Article and Find Full Text PDFJ Org Chem
June 2021
Department of Organic Chemistry, Faculty of Science, Palacký University, Olomouc 779 00, Czech Republic.
Herein, we report the synthesis of skeletally different triazolo[1,5-][1,4]diazepines starting from immobilized homoazidoalanine. After sulfonylation with 2/4-nitrobenzenesulfonyl chlorides and Mitsunobu alkylation with various alkynols, the corresponding -substituted nitrobenzenesulfonamides were obtained. Their catalyst-free Huisgen cycloaddition provided immobilized and functionalized triazolo[1,5-][1,4]diazepines as the key intermediates for further modification.
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