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Preparation of Thioamide Building Blocks via Microwave-Promoted Three-Component Kindler Reactions

Oleksandr I. Zubruyev, Nikola Stiasni and C. Oliver Kappe*

*Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Email: oliver.kappeuni-graz.at

O. I. Zubruyev, N. Stiasni, C. O. Kappe, J. Comb. Chem., 2003, 5, 145-148.

DOI: 10.1021/cc0200538 (free Supporting Information)


Abstract

A microwave-enhanced Kindler thioamide synthesis is introduced. The three-component condensations of aldehydes, amines, and elemental sulfur were carried out using 1-methyl-2-pyrrolidone (NMP) as solvent employing microwave flash heating at 110-180C for 2-20 min. A simple workup protocol allows the isolation of synthetically valuable thioamide building blocks in good yield and purity.

R R', R'' Aldehyde/Amine/S*
(mmol, *S: 32 g/mol)
T (C) t (min) Yield (%, isol.)
 
Ph -(CH2)5- 4/6/5 110 3 95
4-(NO2)Ph -(CH2)5- 4/6/5 130 2 94
PhCH2 -(CH2)5- 4/5/4.5 100 3 73
3-indolyl -(CH2)5- 4/5/4.5 100 8 72
Ph H, PhCH2CH2 4/5/4.5 180 4 99
3,4-(MeO)Ph H, PhCH2CH2 4/5/4.5 140 10 99
4-(NMe2)Ph H, PhCH2CH2 4/5/4.5 140 12 99
3-(Cl)Ph H, PhCH2CH2 4/5/4.5 140 12 97
3-(NO2)Ph H, PhCH2CH2 4/5/4.5 150 10 99
2-(Me)Ph H, PhCH2CH2 4/5/4.5 160 20 43
2-thiophenyl H, PhCH2CH2 4/5/4.5 140 14 99
pentyl H, PhCH2CH2 4/5/4.5 140 12 39
4-(NMe2)Ph H, 2-(MeO)PhCH2CH2 4/5/4.5 140 12 99
3-(Me)Ph H, 2-(MeO)PhCH2CH2 4/5/4.5 140 12 99
3-indolyl H, 2-(MeO)PhCH2CH2 4/5/4.5 140 10 99
Ph H, propyl 4/5/4.5 150 5 93
4-(NMe2)Ph H, propyl 4/5/4.5 170 7 97
3-(Cl)Ph H, propyl 4/5/4.5 140 12 90
3-(NO2)Ph H, propyl 4/5/4.5 150 12 95
pentyl H, propyl 4/5/4.5 140 10 54
Ph H, H 4/6/4.5 180 20 44
4-(Me)Ph H, H 4/6/4.5 170 20 36
3-(Cl)Ph H, H 4/6/4.5 170 20 46
4-(NMe2)Ph H, H 4/6/4.5 160 20 38

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Key Words

Kindler Reaction, Kindler Thioamide Synthesis, Thioamides, Microwave Synthesis, Multicomponent Reactions


ID: JXX-Y2003-1230