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1.
J Org Chem ; 88(16): 11450-11459, 2023 Aug 18.
Article in English | MEDLINE | ID: mdl-37505995

ABSTRACT

A three-component reaction catalyzed by base was established, which mainly consisted of ynals, isocyanates, amines and alcohols. This strategy provides a wide range of substrates and represents a simple process for the preparation of different pyridine derivatives in good yields with high regioselectivities.

2.
J Org Chem ; 88(1): 27-38, 2023 Jan 06.
Article in English | MEDLINE | ID: mdl-36563287

ABSTRACT

A simple and efficient synthetic strategy from amides, ynals, and sodium sulfinates via a Lewis acid-promoted three-component reaction has been reported. Thus, a broad range of various aryl (not alkyl)-substituted oxazoles could be synthesized via the formation of C-N, C-O, and C-S bonds in a one-pot process. In addition, this reaction possesses other unique advantages, such as transition metal-free catalysis, high step economy, good functional group tolerance, and good regioselectivity.

3.
J Org Chem ; 87(11): 7056-7063, 2022 Jun 03.
Article in English | MEDLINE | ID: mdl-35588496

ABSTRACT

An efficient and metal-free approach to the construction of diverse functionalized furan derivatives has been developed from ene-yne-ketones and 1,3,5-triazinanes. As an atom-economical and environment-friendly protocol, the new conditions are suitable for selective C-N and C-O bond formation of a wide range of polysubstituted furans in one pot.

4.
J Org Chem ; 85(23): 14954-14962, 2020 12 04.
Article in English | MEDLINE | ID: mdl-33147029

ABSTRACT

The first example of controllable site-selective pathways to construct 4- and 5-hydroxyalkyl-substituted imidazoles through a three-component reaction of amidines, ynals, and water has been documented. Particularly, the high regioselectivity of the reaction was simply switched by changing the additives. In addition, further 18O-labeled experiments to probe a plausible mechanism and the gram-scale synthesis were studied.

5.
J Org Chem ; 85(15): 10118-10124, 2020 Aug 07.
Article in English | MEDLINE | ID: mdl-32610902

ABSTRACT

A novel and straightforward strategy for the synthesis of functionalized thiazoles from thioamides, ynals, and alcohols via a copper(I)-catalyzed three-component reaction has been described. Through the formation of new C-S, C-N, and C-O bonds in one pot, it is easy to produce various valuable thiazoles fixed with aryl or heteroaryl groups. In addition, the reaction also exhibits other unique advantages, such as high step economics, good functional group tolerance, and good regioselectivity.

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