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Article

De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization †

by
Kazuya Ito
1,
Takayuki Doi
1 and
Hirokazu Tsukamoto
1,2,*
1
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan
2
Department of Pharmaceutical Sciences, Yokohama University of Pharmacy, 601 Matano-cho, Totsuka-ku, Yokohama 245-0066, Japan
*
Author to whom correspondence should be addressed.
†
This paper is dedicated to late Professor Jiro Tsuji.
Catalysts 2023, 13(2), 319; https://doi.org/10.3390/catal13020319
Submission received: 29 December 2022 / Revised: 20 January 2023 / Accepted: 24 January 2023 / Published: 1 February 2023
(This article belongs to the Special Issue Theme Issue in Memory to Prof. Jiro Tsuji (1927–2022))
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Abstract

We report an efficient method to prepare polysubstituted 3-hydroxypyridines from amino acids, propargyl alcohols, and arylboronic acids. The process involves Pd(0)-catalyzed anti-selective arylative cyclizations of N-propargyl-N-tosyl-aminoaldehydes with arylboronic acids (“anti-Wacker”-type cyclization), oxidation of the resulting 5-substituted-3-hydroxy-1,2,3,6-tetrahydropyridines to 3-oxo derivatives, and elimination of p-toluenesulfinic acid. This method provides diverse polysubstituted 3-hydroxypyridines, whose hydroxy group can be further substituted by a cross-coupling reaction via a triflate.
Keywords: “anti-Wacker”-type cyclization; 3-hydroxypyridine; arylboronic acids; palladium; amino acids; propargyl alcohols “anti-Wacker”-type cyclization; 3-hydroxypyridine; arylboronic acids; palladium; amino acids; propargyl alcohols
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MDPI and ACS Style

Ito, K.; Doi, T.; Tsukamoto, H. De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization. Catalysts 2023, 13, 319. https://doi.org/10.3390/catal13020319

AMA Style

Ito K, Doi T, Tsukamoto H. De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization. Catalysts. 2023; 13(2):319. https://doi.org/10.3390/catal13020319

Chicago/Turabian Style

Ito, Kazuya, Takayuki Doi, and Hirokazu Tsukamoto. 2023. "De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization" Catalysts 13, no. 2: 319. https://doi.org/10.3390/catal13020319

APA Style

Ito, K., Doi, T., & Tsukamoto, H. (2023). De Novo Synthesis of Polysubstituted 3-Hydroxypyridines Via “Anti-Wacker”-Type Cyclization. Catalysts, 13(2), 319. https://doi.org/10.3390/catal13020319

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