Citraconic acid and its anhydride-based hetero-Diels-Alder reactions in the synthesis of new thiopyrano[2,3-d][1,3]thiazole derivatives

被引：4

作者：

Zelisko, Nataliya ^{[1
]}

Karpenko, Olexandr ^{[2
]}

Muzychenko, Volodymyr ^{[1
]}

Gzella, Andrzej ^{[3
]}

Lesyk, Roman ^{[1
,4
]}

机构：

[1] Danylo Halytsky Lviv Natl Med Univ, Dept Pharmaceut Organ & Bioorgan Chem, Pekarska 69, UA-79010 Lvov, Ukraine

[2] Enamine Ltd, Kiev, Ukraine

[3] Poznan Univ Med Sci, Dept Organ Chem, Poznan, Poland

[4] Univ Informat Technol & Management Rzeszow, Fac Med, Dept Publ Hlth Dietet & Lifestyle Disorders, Rzeszow, Poland

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 06期

关键词：

Hetero-Diels-Alder reaction; tandem reactions: thiopyrano[2,3-d][1,3]thiazoles; 4-thioxo-2-thiazolidinones;

D O I：

10.1080/00397911.2020.1867868

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel rel-(5R,5aR,11bS)-5-methyl-2,6-dioxo-3,5a,6,11b-tetrahydro-2H,5H-chromeno[4GREEK TONOS,3GREEK TONOS:4,5]thiopyrano[2,3-d][1,3]thiazole-5-carboxylic acids were synthesized in 63-72% yields via tandem acylation-hetero-Diels-Alder reaction of 5-(2-hydroxybenzylidene)-4-thioxo-2-thiazolidinones with citraconic acid and its anhydride. The regio- and stereochemistry of the process was confirmed by NMR spectral data and a single-crystal X-ray diffraction analysis. [GRAPHICS] .

引用

页码：964 / 970

页数：7

共 25 条

[1] Highly diastereoselective Diels-Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone [J].

Adams, Harry ;

Jones, Simon ;

Ojea-Jimenez, Isaac .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2296-2303

[2]

Allen F.H., 1987, J CHEM SOC PERKIN T, VII

[3]

[Anonymous], 1974, J PRAKT CHEM, DOI DOI 10.1002/PRAC.19743160206

[4] Hetero-Diels-Alder reactions of enaminothione with electrophilic olefins.: Synthesis of 2-furyl substituted 2H-thiopyrans [J].

Bogdanowicz-Szwed, K ;

Budzowski, A .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2002, 57 (06) :637-644

[5]

Boger D.L., 1987, HETERODIELS ALDER ME

[6] STUDIES ON SYNTHESIS AND SPECTROSCOPIC PROPERTIES OF NEW TETRAHYDROTHIOPYRANO[2,3-D]-THIAZOLE-DERIVATIVES [J].

EAD, HAR ;

KASSAB, NAL ;

KOPPEL, H ;

BLOEDORN, WD ;

SCHLEINITZ, KD .

JOURNAL FUR PRAKTISCHE CHEMIE, 1980, 322 (01) :155-160

[7] Tandem inverse-electron-demand hetero-/retro-Diels-Alder reactions for aromatic nitrogen heterocycle synthesis [J].

Foster, Radleigh A. A. ;

Willis, Michael C. .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (01) :63-76

[8]

Grishchuk, 1967, CHEM ABSTR, V68, P664

[9]

JONES S, 2001, TETRAHEDRON ASYMM, V12

[10] Synthesis of substituted 3-furan-2(5H)-ones via an anthracene Diels-Alder sequence [J].

Jones, Simon ;

Wilson, Ian .

TETRAHEDRON LETTERS, 2006, 47 (26) :4377-4380

← 1 2 3 →