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Amarendar Maddirala Dissertation.pdf (3.28 MB)

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Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products

Maddirala, Amarendar Reddy
http://rave.ohiolink.edu/etdc/view?acc_num=toledo1461775415

Abstract Details

2016, Doctor of Philosophy, University of Toledo, Chemistry.
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.
Peter Andreana, Ph.D. (Committee Chair)
Joseph Schmidt, Ph.D. (Committee Member)
Jianglong Zhu, Ph.D. (Committee Member)
Liyanaaratchige Tillekeratne, Ph.D. (Committee Member)
180 p.
Chemistry
Multicomponent; oxindole; xenortide; trasamidation

Recommended Citations

Citations

  • Maddirala, A. R. (2016). Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products [Doctoral dissertation, University of Toledo]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1461775415

    APA Style (7th edition)

  • Maddirala, Amarendar Reddy. Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products. 2016. University of Toledo, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=toledo1461775415.

    MLA Style (8th edition)

  • Maddirala, Amarendar Reddy. "Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products." Doctoral dissertation, University of Toledo, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1461775415

    Chicago Manual of Style (17th edition)

toledo1461775415
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This open access ETD is published by University of Toledo and OhioLINK.