Cover
Half Title
De Gruyter Series in Green Bioactive Heterocycles
Green Bioactive Heterocycles: Volume 5
Multicomponent Synthesis: Bioactive Heterocycles
Copyright
Preface
Foreword
A brief professional profile of Prof. Eric F.V. Scriven
Contents
List of contributing authors
1. Synthesis of aza-heterocycles via one-pot domino multicomponent reaction approach
1.1 Introduction
1.2 Synthesis of aza-heterocycles via one-pot domino MCR
1.2.1 Synthesis of nonfused aza-heterocycles
1.2.1.1 Pyrrole and its analogs
1.2.1.2 Pyrazole and its analogs
1.2.1.3 Imidazole and its analogs
1.2.1.4 Tetrazole and its analogs
1.2.1.5 Isoxazole and its analogs
1.2.1.6 Thiazolidine derivatives
1.2.1.7 Pyridine and its analogs
1.2.1.8 Pyrimidine and its analogs
1.2.2 Fused aza-heterocycles
1.2.2.1 Indole and its analogs
1.2.2.2 Pyrrole fused aza-heterocycles
1.2.2.3 Pyrazole-fused aza-heterocycles
1.2.2.4 Imidazole-fused aza-heterocycles
1.2.2.4.1 Benzimidazoles
1.2.2.4.2 Imidazopyridines
1.2.2.5 Quinoline and its analogs
1.2.2.6 Quinazoline and its analogs
References
2. One-pot three-component selective annulation strategies for the synthesis of bioactive β-lactam, pyrrole, and pyridine scaffolds
2.1 Introduction
2.2 Three-component synthesis of β-lactams
2.2.1 Using Ugi reaction
2.2.2 Using Kinugasa reaction
2.2.3 Using Staudinger reaction
2.3 Three-component synthesis of pyrroles
2.3.1 From 1,3-dicarbonyl compounds
2.3.2 From alkynes
2.3.3 From carbonyl compounds
2.3.4 From α,β-unsaturated carbonyls (α,β-UC)
2.3.5 Miscellaneous
2.4 Three-component synthesis of pyridine
References
3. One-pot three-component synthesis of quinolines and some other selective six-membered heterocycles with biological importance
3.1 Introduction
3.2 Nitrogen-containing heterocycles
3.2.1 Quinoline derivatives
3.2.1.1 Synthesis of 3-arylsulfonylquinolines via cascade oxidative coupling
3.2.1.2 Synthesis of 3-arylquinolines via [3+1+1+1] annulation
3.2.1.3 Regioselective synthesis of substituted quinolines
3.2.1.4 Metal-free synthesis of 4-arylquinolines
3.2.1.5 An iron(III)-catalyzed synthesis of 2-pyridones
3.2.1.6 Solid-state synthesis of chromenopyridinones
3.2.1.7 Ball-milling approach of pyridocoumarin synthesis
3.2.2 Pyrimidines and quinazolines
3.2.2.1 Microwave-assisted synthesis of quinazolino[4,3-b]quinazolin-8-ones
3.2.2.2 I2/CuCl2 copromoted synthesis of 2-acyl-4-aminoquinazolines
3.2.2.3 Synthesis of 2,4-substituted quinazolines
3.2.2.4 Synthesis of 5H-chromeno[2,3-d]pyrimidin-5-one derivatives
3.2.2.5 Synthesis of 2,4,6-trisubstituted pyrimidines
3.2.2.6 Synthesis of imidazo[1,2-a]pyrimidines
3.2.3 1,4-Dihydropyridines (DHPs)
3.2.3.1 Metal-free synthesis of Hantzsch 1,4-dihydropyridines
3.2.3.2 Divergent synthesis of dual 1,4-dihydropyridines
3.2.4 Naphthyridines
3.2.4.1 Synthesis of substituted benzo[c]pyrazolo[2,7]naphthyridines
3.2.4.2 Ultrasonic-promoted synthesis of 1,6-naphthyridine
3.2.5 Spiro-heterocycles
3.2.5.1 Synthesis of indol-fused dispiro-heterocycles
3.2.5.2 Synthesis of spirooxindoles fused pyrazolo-tetrahydropyridinone and coumarin-dihydropyridine-pyrazole
3.3 Oxygen and sulfur-containing heterocycles
3.3.1 Pyran
3.3.1.1 Synthesis of pyrano[3,2-c]quinolone derivatives
3.3.1.2 Synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3-d]pyrimidinones
3.3.2 Oxazines
3.3.2.1 Synthesis of 1,3,5-oxadiazines
3.3.2.2 Synthesis of coumarin fused bis-oxazines
3.3.3 Thiazine
3.3.3.2 Synthesis of naphtho[1,2-e]/benzo[e][1,3]thiazine derivatives
3.3.3.1 Synthesis of 1,3-thiazine-4-ones
3.4 Conclusion
References
4. Multicomponent synthesis of biologically prominent tetrahydrobenzoxanthenone derivatives
4.1 Introduction
4.2 Homogeneous catalyst reported for benzoxanthenone derivative synthesis
4.2.1 Reported biological studies
4.3 Heterogeneous catalyzed reactions
4.3.1 Reported biological activities
4.4 Conclusions
Abbreviations
References
5. One-pot five/four-component synthesis of structurally diverse bioactive quinoxaline-annulated spiroheterocycles through the in situ formation of 11H-indeno[1,2-b]quinoxalin-11-ones
5.1 Introduction
5.2 Five-component synthesis of quinoxaline annulated spiroheterocycles
5.2.1 Five-component synthesis of spiro-pyrrolidines
5.2.2 Five-component synthesis of dispiro-pyrrolidines
5.3 Four-component synthesis of quinoxaline annulated spiroheterocycles
5.3.1 Four-component synthesis of spiro-pyrrolidine
5.3.2 Four-component synthesis of ferrocene-embedded spiropyrrolidine
5.3.3 Four-component synthesis of dispiro-indenoquinoxalines
5.3.4 Four-component synthesis of spiro-indenoquinoxalines
5.3.5 Four-component synthesis of spiropyrans–indenoquinoxalines
5.3.6 Four-component synthesis of spirofuran–indenoquinoxalines
5.4 Conclusions
References
6. Multicomponent synthesis of biologically active quinazolinone derivatives
6.1 Introduction
6.2 Biological applications
6.3 Chemical synthesis of quinazolinone derivatives
6.4 Conclusion
Abbreviations
References
7. Recent approaches toward the synthesis of 1,2,3-triazoles using multicomponent techniques
7.1 Introduction
7.2 The 1,2,3-triazole synthesis by three-component reaction
7.2.1 Three-component coupling among alkyl halide, terminal alkyne, and sodium azide
7.2.2 Three-component coupling among alkyl or aryl boronic acid, terminal alkyne or alkynyl carboxylic acid, and sodium azide
7.2.3 Three-component coupling among α-keto acetal, tosyl hydrazine, and primary amine
7.2.4 Three-component coupling among N-propargyl ortho-bromo benzamide, alkyl halide, and alkyl azide
7.2.5 Three-component coupling among aldehyde, nitroalkene, or nitroalkane and sodium azide
7.2.6 Three-component coupling among o-phenylenediamine, 2-azidobenzaldehyde, and arylchalcogenyl alkynes
7.2.7 Three-component coupling among epoxide, terminal alkyne, and sodium azide
7.2.8 Three-component coupling reaction among isatin Schiff base, sulfonamide, and aromatic aldehyde
7.2.9 Three-component coupling reaction of 2H-azirine, terminal alkyne, and sodium azide
7.2.10 Three-component coupling reaction of diazomethane sulfonamides, primary aliphatic amines, and aromatic aldehydes
7.2.11 Three-component coupling reaction of α-CF3 carbonyls (both ketone and ester), aryl azides, and amines
7.3 Four-component coupling reaction for triazole synthesis
7.3.1 Four-component coupling reaction 2-azidobenzenamines, aldehydes, propiolic acids, and isocyanides
7.3.2 Four-component coupling reaction among terminal alkyne, urea, α-azido ketone, and aromatic aldehyde
7.3.3 Four-component coupling reaction among acid chloride, TIPS-protected 1,3-butadiyne, hydrazine, and alkyl azide
7.4 Five-component coupling reaction for triazole synthesis
7.4.1 Five-component coupling reaction among indole, aromatic aldehyde, propargyl bromide, alkyl halide, and NaN3
7.4.2 Five-component coupling reaction via Ugi-4CR approach
7.4.3 Five-component coupling reaction of N-propargyl isatins, malononitrile, 4-hydroxycarbazole, aralkyl halides, and sodium azide
7.5 Conclusion
List of abbreviation
References
8. Synthesis of various bioactive tetrazoles via one-pot multicomponent click reactions
8.1 Introduction
8.2 Recent literature reports
8.3 Conclusions
References
9. L-Proline and its derivatives catalyzed one-pot multicomponent synthesis of biologically promising N- and O-heterocycles
9.1 Introduction
9.2 Why proline prefers as a good organocatalysts among other natural
9.3 L-Proline-catalyzed synthesis of N-heterocycles
9.3.1 L-proline derivative-catalyzed N-heterocycle synthesis
9.3.2 Synthesis of N-heterocycle by using L-proline-supported catalysts
9.3.3 L-Proline-catalyzed synthesis of O-heterocycles
9.3.4 Proline derivatives catalyzed synthesis of O-heterocycle
9.3.5 Proline-supported catalyzed O-heterocycle synthesis
9.4 Conclusion
Abbreviations
References
10. Microwave-assisted solvent-free multicomponent synthesis of bioactive heterocycles
10.1 Introduction
10.2 Multicomponent reactions
10.3 Microwave-assisted synthesis of solvent-free multicomponent synthesis of heterocycles
10.3.1 Acridone derivatives
10.3.2 Pyrimidine derivatives
10.3.3 Imidazole and fused imidazole derivatives
10.3.4 Pyrrole and fused pyrrole derivatives
10.3.5 Pyridine derivatives
10.3.6 Nitrogen–sulfur heterocycles
10.3.7 Oxygen heterocycles
10.3.8 Spiroheterocycles
10.3.9 Fused bicyclic heterocycles
10.3.10 MW-assisted solvent-free MCR synthesis of heterocycles using catalyst
10.4 Conclusions
References
11. Deep eutectic mixture (DEM)-assisted multicomponent synthesis of heterocycles
11.1 Introduction
11.2 Deep eutectic mixtures (DEMs) as reaction media-cum-catalyst in multicomponent synthesis of heterocycles
11.2.1 Synthesis of spirooxindole and pyrano [2,3-c] pyrazole derivatives
11.2.2 Synthesis of chromene, pyrrole, and α-acyloxyamide derivatives
11.2.3 Synthesis of quinoline, imidazo pyridine, pyrazole, and Betti base derivatives
11.2.4 Synthesis of chromyl phosphate, dihydropyrimidinone, pyrazolopyridine, and pyrazolophthalazine
11.2.5 Synthesis of spirooxindolopyran, spirooxindoloxanthenes, aminobenzochromene, decahydroacridine, chromenopyridine, tetrahydrobenzopyran, and hexahydroxenthene -dione derivatives
11.2.6 Synthesis of pyranopyrimidinone, dihydropyridopyrimidine, and alkylidienethiazolone derivatives
11.3 Deep eutectic mixtures (DEMs) as catalyst with conventional reaction media in multicomponent synthesis of heterocycles
11.3.1 Synthesis of spirodioxoloquinolinepyrimidine, spiropyrazoloquinolinepyrimidine, and pyrazolopyrimidoquinoline derivatives
11.3.2 Synthesis of tetrahydrodipyrazolo pyridine, pyrrole, β-amino ketones, 2-aminochromene, and pyranocoumarin derivatives
11.4 Deep eutectic mixture (DEM)-compatible metallic catalysts in multicomponent synthesis of heterocycles
11.4.1 Synthesis of 3-aminobenzofuran, β-aminoketones, and imidazole derivatives
11.4.2 Synthesis of thieno indoles, aryl ether, and aryl amine derivatives
11.5 Conclusions
References
Index