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Chapter 1: Part 1: A Unique Approach of Preparing 3,3-Disubstituted Oxindoles from Acyclic Tetrasubstituted Aldehydes: Total Synthesis of (-)-Coerulescine and (-)-Coixspirolactam A, Chapter 1: Part 2: Synthetic Scope of Bronsted Acid Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate, Chapter 2: Investigation of the C2‐Alkylation of 1‐(1H‐Indol‐3‐yl)‐N,N-Dimethylmethanamine.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Chapter 1: Part 1: A Unique Approach of Preparing 3,3-Disubstituted Oxindoles from Acyclic Tetrasubstituted Aldehydes: Total Synthesis of (-)-Coerulescine and (-)-Coixspirolactam A, Chapter 1: Part 2: Synthetic Scope of Bronsted Acid Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate, Chapter 2: Investigation of the C2‐Alkylation of 1‐(1H‐Indol‐3‐yl)‐N,N-Dimethylmethanamine./
Author:	Ali, Md Shahnawaz.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2021,
Description:	374 p.
Notes:	Source: Dissertations Abstracts International, Volume: 83-01, Section: B.
Contained By:	Dissertations Abstracts International83-01B.
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28540745
ISBN:	9798516078743

Chapter 1: Part 1: A Unique Approach of Preparing 3,3-Disubstituted Oxindoles from Acyclic Tetrasubstituted Aldehydes: Total Synthesis of (-)-Coerulescine and (-)-Coixspirolactam A, Chapter 1: Part 2: Synthetic Scope of Bronsted Acid Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate, Chapter 2: Investigation of the C2‐Alkylation of 1‐(1H‐Indol‐3‐yl)‐N,N-Dimethylmethanamine.
Ali, Md Shahnawaz.

Chapter 1: Part 1: A Unique Approach of Preparing 3,3-Disubstituted Oxindoles from Acyclic Tetrasubstituted Aldehydes: Total Synthesis of (-)-Coerulescine and (-)-Coixspirolactam A, Chapter 1: Part 2: Synthetic Scope of Bronsted Acid Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate, Chapter 2: Investigation of the C2‐Alkylation of 1‐(1H‐Indol‐3‐yl)‐N,N-Dimethylmethanamine. - Ann Arbor : ProQuest Dissertations & Theses, 2021 - 374 p.

Source: Dissertations Abstracts International, Volume: 83-01, Section: B.

Thesis (Ph.D.)--The University of Wisconsin - Milwaukee, 2021.

This item must not be sold to any third party vendors.

CHAPTER 1: PART A: A UNIQUE APPROACH OF PREPARING 3,3-DISUBSTITUTED OXINDOLES FROM ACYCLIC TETRASUBSTITUTED ALDEHYDES: TOTAL SYNTHESIS OF (-)-COERULESCINE AND (-)-COIXSPIROLACTAM A(-)-Coerulescine and (-)-coixspirolactam A, two naturally occurring compounds characterized with an all-carbon quaternary center containing a spirooxindole, have been synthesized asymmetrically. The key feature of their total synthesis involves a novel rational construction of the chiral 3,3-disubstituted oxindole core from the acyclic chiral tetrasubstituted aldehyde. The later scaffold was prepared in high enantioselectivity (up to 86%) from the ethyl 3-hydroxy-2-(2-nitrophenyl)acrylate 1 by exploring both intermolecular and intramolecular Pd-mediated asymmetric allylic allylations (Pd-AAA). A through optimization of these approaches is described in this thesis.CHAPTER 1: PART B: SYNTHETIC SCOPE OF BRONSTED ACID CATALYZED REACTIONS OF CARBONYL COMPOUNDS AND ETHYL DIAZOACETATEThe comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Bronsted acid catalyst is described. In this, a broad range of 3-oxo esters were synthesized from a variety of ketones, specifically benzophenones and aliphatic ketones. For the diaryl ketones, we have characterized two inseparable products of migration by two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and calculated the ratio of their relative migratory tendencies. However, the symmetric and nonsymmetrical aliphatic ketones provided the higher migration for relatively longer alkyl chains length. In case of the aliphatic aldehydes, we got exclusively the expected β-keto ester by a 1,2- hydride shift.CHAPTER 2: INVESTIGATION OF THE C2-ALKYLATION OF 1-(1H-INDOL-3-YL)-N,N-DIMETHYLMETHANAMINEIndole derivatives can be conveniently alkylated at the C2 position by choosing appropriate N-protecting group and appropriate base. However, 1-(1H-indol-3-yl)-N,N-dimethylmethanamine (commercially named as gramine) is also limited to that restricted choice of a protecting group for such alkylation. Herein we explore a the lithiation of gramine with different protecting groups (such as Ms, Ts, Me, TIPS etc.) on the N-heteroatom and investigate the alkylation at the C-2 position by trapping the C-2 lithio species with a variety of electrophiles such as methyl iodide, benzyl bromide, prenyl bromide, allyl bromide, etc.

ISBN: 9798516078743Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

3-disubstituted oxindole

Chapter 1: Part 1: A Unique Approach of Preparing 3,3-Disubstituted Oxindoles from Acyclic Tetrasubstituted Aldehydes: Total Synthesis of (-)-Coerulescine and (-)-Coixspirolactam A, Chapter 1: Part 2: Synthetic Scope of Bronsted Acid Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate, Chapter 2: Investigation of the C2‐Alkylation of 1‐(1H‐Indol‐3‐yl)‐N,N-Dimethylmethanamine.
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035 $a (MiAaPQ)AAI28540745
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100 1 $a Ali, Md Shahnawaz. $0 (orcid)0000-0001-8857-636X $3 3686368
245 1 0 $a Chapter 1: Part 1: A Unique Approach of Preparing 3,3-Disubstituted Oxindoles from Acyclic Tetrasubstituted Aldehydes: Total Synthesis of (-)-Coerulescine and (-)-Coixspirolactam A, Chapter 1: Part 2: Synthetic Scope of Bronsted Acid Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate, Chapter 2: Investigation of the C2‐Alkylation of 1‐(1H‐Indol‐3‐yl)‐N,N-Dimethylmethanamine.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2021
300 $a 374 p.
500 $a Source: Dissertations Abstracts International, Volume: 83-01, Section: B.
500 $a Advisor: Hossain, M. Mahmun.
502 $a Thesis (Ph.D.)--The University of Wisconsin - Milwaukee, 2021.
506 $a This item must not be sold to any third party vendors.
520 $a CHAPTER 1: PART A: A UNIQUE APPROACH OF PREPARING 3,3-DISUBSTITUTED OXINDOLES FROM ACYCLIC TETRASUBSTITUTED ALDEHYDES: TOTAL SYNTHESIS OF (-)-COERULESCINE AND (-)-COIXSPIROLACTAM A(-)-Coerulescine and (-)-coixspirolactam A, two naturally occurring compounds characterized with an all-carbon quaternary center containing a spirooxindole, have been synthesized asymmetrically. The key feature of their total synthesis involves a novel rational construction of the chiral 3,3-disubstituted oxindole core from the acyclic chiral tetrasubstituted aldehyde. The later scaffold was prepared in high enantioselectivity (up to 86%) from the ethyl 3-hydroxy-2-(2-nitrophenyl)acrylate 1 by exploring both intermolecular and intramolecular Pd-mediated asymmetric allylic allylations (Pd-AAA). A through optimization of these approaches is described in this thesis.CHAPTER 1: PART B: SYNTHETIC SCOPE OF BRONSTED ACID CATALYZED REACTIONS OF CARBONYL COMPOUNDS AND ETHYL DIAZOACETATEThe comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Bronsted acid catalyst is described. In this, a broad range of 3-oxo esters were synthesized from a variety of ketones, specifically benzophenones and aliphatic ketones. For the diaryl ketones, we have characterized two inseparable products of migration by two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and calculated the ratio of their relative migratory tendencies. However, the symmetric and nonsymmetrical aliphatic ketones provided the higher migration for relatively longer alkyl chains length. In case of the aliphatic aldehydes, we got exclusively the expected β-keto ester by a 1,2- hydride shift.CHAPTER 2: INVESTIGATION OF THE C2-ALKYLATION OF 1-(1H-INDOL-3-YL)-N,N-DIMETHYLMETHANAMINEIndole derivatives can be conveniently alkylated at the C2 position by choosing appropriate N-protecting group and appropriate base. However, 1-(1H-indol-3-yl)-N,N-dimethylmethanamine (commercially named as gramine) is also limited to that restricted choice of a protecting group for such alkylation. Herein we explore a the lithiation of gramine with different protecting groups (such as Ms, Ts, Me, TIPS etc.) on the N-heteroatom and investigate the alkylation at the C-2 position by trapping the C-2 lithio species with a variety of electrophiles such as methyl iodide, benzyl bromide, prenyl bromide, allyl bromide, etc.
590 $a School code: 0263.
650 4 $a Organic chemistry. $3 523952
650 4 $a Chemistry. $3 516420
650 4 $a Chemical engineering. $3 560457
653 $a 3-disubstituted oxindole
653 $a All carbon quaternary center
653 $a Asymmetric synthesis
653 $a C2-alkylation
653 $a Coixspirolactam A
653 $a Pd-AAA
690 $a 0490
690 $a 0485
690 $a 0542
710 2 $a The University of Wisconsin - Milwaukee. $b Chemistry. $3 2100361
773 0 $t Dissertations Abstracts International $g 83-01B.
790 $a 0263
791 $a Ph.D.
792 $a 2021
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28540745