Rongalite-mediated one-pot aminomethylation of heteroarenes using secondary amines/anilines has been developed. This transition-metal-free and mild reaction offers an efficient way to synthesize aminomethylated heteroaromatic compounds with high yields and broad functional group tolerance. Here, Rongalite plays a key role in generating the C1 unit source , which triggers the aminomethylation process. This approach provides a library of aminomethylated imidazo[1,2-]pyridines and imidazo[2,1-]thiazoles.
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http://dx.doi.org/10.1021/acs.joc.4c02050 | DOI Listing |
J Org Chem
December 2024
Department of Chemistry, National Institute of Technology Warangal, Warangal, Telangana 506004, India.
Rongalite-mediated one-pot aminomethylation of heteroarenes using secondary amines/anilines has been developed. This transition-metal-free and mild reaction offers an efficient way to synthesize aminomethylated heteroaromatic compounds with high yields and broad functional group tolerance. Here, Rongalite plays a key role in generating the C1 unit source , which triggers the aminomethylation process.
View Article and Find Full Text PDFChem Sci
July 2024
Los Alamos National Laboratory Los Alamos New Mexico 87545 USA
A geometrically flexible bifunctional (bis)aminophosphine ligand was synthesized in a three-component, one-pot Kabachnik-Fields reaction using butylphosphine, paraformaldehyde, and 3,5-dimethyl aniline. The product, bis((3,5-dimethylphenyl)aminomethyl) butylphosphine (BiAMP ), containing two secondary amines and a tertiary phosphine, was isolated in good yields. Deprotonation of both N-H groups with (trimethylsilyl)methylpotassium (K-CHSiMe), followed by salt metathesis with LaI, YI, and LuI generated the corresponding MI(BiAMP )(thf) complexes (M = Y (1), La (2), and Lu (3)) in good yields.
View Article and Find Full Text PDFNat Commun
July 2024
Department of Systems Biotechnology, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul, 05029, Republic of Korea.
Biobased furans have emerged as chemical building blocks for the development of materials because of their diverse scaffolds and as they can be directly prepared from sugars. However, selective, efficient, and cost-effective scalable conversion of biobased furans remains elusive. Here, we report a robust transaminase (TA) from Shimia marina (SMTA) that enables the scalable amination of biobased furanaldehydes with high activity and broad substrate specificity.
View Article and Find Full Text PDFSteroids
August 2024
Laboratory of Medicinal Chemistry, Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentyev Ave, 9, 630090 Novosibirsk, Russian Federation. Electronic address:
Betulonic acid benzyl ester 1 has been subjected to a series of structural modifications for the purpose of new triterpenoid synthesis and evaluating for anticancer activity. The one-pot two step synthesis of 2α-(aminomethyl)betulinic acid benzyl ester derivatives 3a-f (yield 46-69 %) was achieved by the Mannich reaction of compound 1 with methyleneiminium salts, generated in situ from N,N-disubstituted bis(amino)methanes 2a-f by the action of acetyl chloride in dichloromethane, and subsequent reduction of aminomethylation products with sodium borohydride. Minor 2β-(aminomethyl) triterpenoids 4c,d,f were also isolated (yield 6-15 %).
View Article and Find Full Text PDFOrg Biomol Chem
April 2024
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.
The colorless solution of furan-2-yl bis(indolyl)methane (BIM) is newly revealed to work as a palladium (Pd) ion-selective chromogenic agent by turning orange. 5-(-Methyl--phenyl-aminomethyl)-furan-2-yl BIM could be synthesized from 5-chloromethylfurfural as a biorenewable feedstock one-pot and double functionalization, and a mixture of its solution and Pd ions showed the highest absorbance at 465 nm in UV-Vis analysis. On the other hand, other metal ions (Cu, Cr, Cr, Fe, Fe, Ni, Zn, In, Pt, or Ce) exhibited no response.
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