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Review
. 2009 Dec 1;14(12):4936-72.
doi: 10.3390/molecules14124936.

Microwave multicomponent synthesis

Helmut M Hügel  1
Affiliations
Review

Microwave multicomponent synthesis

Helmut M Hügel. Molecules. .

Abstract

In the manner that very important research is often performed by multidisciplinary research teams, the applications of multicomponent reactions involving the combination of multiple starting materials with different functional groups leading to the higher efficiency and environmentally friendly construction of multifunctional/complex target molecules is growing in importance. This review will explore the advances and advantages in microwave multicomponent synthesis (MMS) that have been achieved over the last five years.

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Figures

Scheme 1
Scheme 1
Optimized Biginelli reaction conditions for dihydropyrimidine synthesis.
Scheme 2
Scheme 2
Optimized Biginelli reaction conditions for bromophenyl-substituted DHPM synthesis.
Scheme 3
Scheme 3
Bronsted acid catalyzed Biginelli DHPM synthesis.
Scheme 4
Scheme 4
Biginelli reaction for synthesis of 2-amino-4-arylpyrimidines.
Scheme 5
Scheme 5
Biginelli reaction to 2-thioxopyrimidines and derivatives.
Scheme 6
Scheme 6
The Biginelli reaction route to 2-amino-DHPMs.
Scheme 7
Scheme 7
Generation of 5-aroyl-3,4-dihydropyrimidin-2-one library from Biginelli and Liebeskind-Srogl coupling reactions.
Scheme 8
Scheme 8
The utilization of IL-PEG technology for the Biginelli, Hantzsch reactions.
Scheme 9
Scheme 9
MW-tuning chemo- and regio-selectivity of three-component condensation products.
Scheme 10
Scheme 10
Formation of pyrazoloquinazolinone 5 and pyrazoquinolizinone 6 by three-component-base condensation reactions.
Scheme 11
Scheme 11
Optimized Biginelli-MMS of Monastrol.
Scheme 12
Scheme 12
The asymmetric Biginelli-MMS.
Scheme 13
Scheme 13
The Ugi reaction: The effects of MW, solvents, bifunctional substrates.
Scheme 14
Scheme 14
Ugi MMS to racemic 1,4-benzodiazepin-3-ones A or B.
Scheme 15
Scheme 15
Sequential Ugi plus Suzuki coupling to form 2,3,6-trisubstituted imidazo(1,2-a)pyridines.
Scheme 16
Scheme 16
Ugi-MMS with intramolecular O-alkylation furnishing substituted benzoxazines.
Scheme 17
Scheme 17
Ugi-MMS with tandem deprotection/intramolecular N-cyclizations to triazadibenzoazulenones.
Scheme 18
Scheme 18
The UDC-MMS strategy leading to diketopiperazines and 1,4-benzodiazepine-2,5-diones.
Scheme 19
Scheme 19
MMS-MACOS provided a small library of 2-amino furans.
Scheme 20
Scheme 20
Production of pyrazoloquinolinones by Hantzsch-MMS using MACOS in DMSO.
Scheme 21
Scheme 21
Hantzsch-MMS of polyhydroquinolines catalyzed by Ni-nanoparticles.
Scheme 22
Scheme 22
MMS of indolyl-pyridine derivatives.
Scheme 23
Scheme 23
MMS of polycyclic-fused isoxazolpyridines in water.
Scheme 24
Scheme 24
MMS of fuoro- and indeno-pyridopyrimidines in water.
Scheme 25
Scheme 25
Hantzsch-MMS of 4-(C-galactosylmethyl)-2-(alaninyl)pyridine and 2-(C-galactosylmethyl)-4-(alaninyl)pyridine derivatives.
Scheme 26
Scheme 26
MMS of functionalized hexa-substituted 1,4-dihydropyridines.
Scheme 27
Scheme 27
Conventional heating of four-component reaction providing mixtures of hexa-substituted 1,4-dihydropyridines.
Scheme 28
Scheme 28
MMS of naphtha[2,3-f]quinoline derivatives.
Scheme 29
Scheme 29
MMS of polysubstituted imidazo[1,2-a]-quinazolines, pyrimido[1,2-a]-quinolines, quinolino[1,2-a]-quinazolines.
Scheme 30
Scheme 30
The three-component—MW synthesis of Glyantrypine, Fumiquinazoline F and Fiscalin B.
Scheme 31
Scheme 31
Three-component—MW synthesis of Circumdatin E analogues.
Scheme 32
Scheme 32
Three-component - MW synthesis of Isaindigotone.
Scheme 33
Scheme 33
Summary of MMS of the Quinazolin-4-one scaffold.
Scheme 34
Scheme 34
Utilization of MMS in the synthesis of Steganacin aza-analogues.
Scheme 35
Scheme 35
MMS of multiring heterocycles.
Scheme 36
Scheme 36
Alkaloid synthesis via MMS/RCM/Heck reactions.
Scheme 37
Scheme 37
The parallel MMS of imidazothiazol-3-one and imidazothiazin-4-one products.
Scheme 38
Scheme 38
The chemoselective MMS of N-substituted 2-aminopyridines and substituted 2,6-dicyanoanilines.
Scheme 39
Scheme 39
MMS of spiroimidazolinones by one-pot sequential and domino reactions.
Scheme 40
Scheme 40
The synthesis of Irbesartan by a one-pot two-step reaction sequence.
Scheme 41
Scheme 41
Optimized MMS of imidazoles.
Scheme 42
Scheme 42
MMS of piperazinedione-fused tricyclic compounds.
Scheme 43
Scheme 43
MMS products from aldehydes, phenylpyruvic acid and aminoazoles.
Scheme 44
Scheme 44
MMS of the 4-oxotetrahydro-β-carboline scaffold.
Scheme 45
Scheme 45
MMS of a substituted 2-aminochromene.
Scheme 46
Scheme 46
MMS of 2-aminochromenes using Mg/Al catalysis.
Scheme 47
Scheme 47
Zinc chloride catalyzed MMS of 2-amino-3,5-dicarbonitrile-6-thio-pyridines.
Scheme 48
Scheme 48
MMS of coumarin substituted pyridine derivatives.
Scheme 49
Scheme 49
MMS protocols to spirooxindoles.
Scheme 50
Scheme 50
MMS influence by solvent and substituent effects.
Scheme 51
Scheme 51
Solvent-selective MMS of 6-hydroxy-3-pyrimidin-5-yl propanoic acid, 6-hydroxy-3-pyrimidin-5-yl propanamide and spiro [5,5]undecane-1,5,9-triones.
Scheme 52
Scheme 52
MMS of tricyclic thiochromeno[2,3-b]pyridine derivatives.
Scheme 53
Scheme 53
The synthesis of pyrano-1,4-benzoquinone adducts.
Scheme 54
Scheme 54
The MMS of heteropolycyclic compounds.
Scheme 55
Scheme 55
MMS of 2,3-dihydropyrans.
Scheme 56
Scheme 56
MMS approach to furanose-pyranose 1,3-C-C-linked-disaccharides.
Scheme 57
Scheme 57
MMS of N-1, C-6-disubstituted 3,5-dichloro-2(1H)-pyrazinones.
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