A simple and efficient method for the base-mediated synthesis of unsymmetrical 1,3,5-triazin-2-amines has been developed. The protocol uses readily available imidates, guanidines, and amides or aldehydes as the starting materials, cesium carbonate as the base, no catalyst or additive is required, and the three-component reaction provides diverse 1,3,5-triazin-2-amines in moderate to good yields with tolerance of wide functional groups.
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http://dx.doi.org/10.1021/acs.joc.7b01510 | DOI Listing |
Org Lett
January 2025
Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati, Assam 781039, India.
Herein, an organocatalytic asymmetric desymmetrizing [4+2] cycloaddition/base-mediated oxidative aromatization reaction sequence has been developed between spirophthalide 2,5-cyclohexadienones and β-methyl cinnamaldehydes. The reaction proceeds through chiral dienamine intermediate formation, and the densely functionalized spirocyclic isobenzofuranone-embedded chiral arenes were formed in high yields with excellent enantioselectivities. A 2-fold desymmetrization reaction was also performed, and the products were obtained in high enantioselectivities.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Anhui Academy of Science and Technology, HeFei 230088, China.
The expeditious construction of tetrasubstituted furans Cu/base-promoted cascade reactions of terminal alkynes with 1,2-diketones is described. This reaction proceeds smoothly, involving the formation of multiple chemical bonds tolerating a wide range of functional groups. The mechanism underlying these transformations has been thoroughly investigated, suggesting that 1,3-diyne serves as a key intermediate generated through oxidative coupling facilitated by the Cu catalyst.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr Homi Bhabha Road, Pune-411008, India.
We have developed a novel base-mediated method for the selective C3-alkylation of quinoxalin-2(1)-one and -protected quinoxalin-2(1)-one using inexpensive, unactivated nitroalkanes. This approach tolerates a wide range of functional groups and supports the synthesis of various bioactive compounds. Gram-scale reactions demonstrate the scalability of the method.
View Article and Find Full Text PDFRSC Adv
November 2024
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT) Hyderabad 500 007 India
This study presents the design and application of intramolecular arylogous nitroaldol (Henry) condensation. A transition metal-free, base-mediated reaction of -heteroatom-substituted aryl aldehydes/ketones and 2-nitrobenzyl (pseudo)halides has been developed to access a wide range of 2-(2-nitroaryl)benzofuran/2-(2-nitroaryl)indole derivatives in high yields. The reaction appears to proceed through -/-benzylation and intramolecular arylogous nitroaldol condensation.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Fluoro-Agro chemicals Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
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