Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products
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University of Toledo / OhioLINK
2016
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| Online Access: | http://rave.ohiolink.edu/etdc/view?acc_num=toledo1461775415 |
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ndltd-OhioLink-oai-etd.ohiolink.edu-toledo14617754152021-08-03T06:36:12Z Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products Maddirala, Amarendar Reddy Chemistry Multicomponent oxindole xenortide trasamidation Isocyanide-based multicomponent reactions (IBMRs) have great advantages towards the assembly of complex molecules and are concise for the synthesis of higher ordered core structural motifs accomplished in a single synthetic transformation. Complexity generating reactions have become quite useful in assembling molecules containing a variety of stereocenters in an economical and time-saving manner. Particularly, the Ugi four component reaction sequence, followed by a variety of post condensation or transformational modifications allow the synthetic chemist to synthesize many biologically active molecules including those with diverse heterocyclic scaffolds and natural products. Of those types of molecules, 3-substituted-2-indolinone scaffolds have many important functions in biological systems including a wide-range of beneficial activities. From this perspective, the syntheses of 3-substituted-2-indolinones are an interesting target for an organic synthetic chemist to study the applications in medicinal chemistry. Our approach demands the efficient synthesis of 3-substituted-2-indolinones through microwave irradiation and selective intramolecular transamidation of the Ugi four component condensation derivative(s). Additionally, investigation for the ability of symmetrical versus unsymmetrical amine component(s) and carboxylic component(s) to eliminate the formation of rotameric mixtures obtained during the practice, simplifies NMR analysis and allows for further molecular design amplification. Likewise, the synthesis of spiro-[indoline-3,2'-pyrrolidine]-2,5'-diones via post-Ugi-4CR/transamidation/cyclization sequential process has been achieved in three steps in a one-pot reaction using methyl isocyanide as a convertible isocyanide. Variation in the carboxylic acid moiety allows for the generation of new quaternary carbon centers under basic reaction conditions and provides the molecular diversity in a small library of spirocyclic oxindole Γ-lactams. Finally, bioactive natural products, xenortides A-D and their stereoisomers, were synthesized in a one-pot, two-step reaction using the methodology learned from the Ugi four component reaction. 2016 English text University of Toledo / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=toledo1461775415 http://rave.ohiolink.edu/etdc/view?acc_num=toledo1461775415 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws. |
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NDLTD |
| language |
English |
| sources |
NDLTD |
| topic |
Chemistry Multicomponent oxindole xenortide trasamidation |
| spellingShingle |
Chemistry Multicomponent oxindole xenortide trasamidation Maddirala, Amarendar Reddy Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products |
| author |
Maddirala, Amarendar Reddy |
| author_facet |
Maddirala, Amarendar Reddy |
| author_sort |
Maddirala, Amarendar Reddy |
| title |
Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products |
| title_short |
Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products |
| title_full |
Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products |
| title_fullStr |
Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products |
| title_full_unstemmed |
Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products |
| title_sort |
applications of ugi four component cascade coupling reactions for the synthesis of bioactive diverse heterocyclic molecules and natural products |
| publisher |
University of Toledo / OhioLINK |
| publishDate |
2016 |
| url |
http://rave.ohiolink.edu/etdc/view?acc_num=toledo1461775415 |
| work_keys_str_mv |
AT maddiralaamarendarreddy applicationsofugifourcomponentcascadecouplingreactionsforthesynthesisofbioactivediverseheterocyclicmoleculesandnaturalproducts |
| _version_ |
1719440280011145216 |