Asset Details
Do you wish to reserve the book?
New avenues towards synthesis and applications of amino acid derived heterocycles
Hey, we have placed the reservation for you!
By the way, why not check out events that you can attend while you pick your title.
Oops! Something went wrong.
Looks like we were not able to place the reservation. Kindly try again later.
Are you sure you want to remove the book from the shelf?
New avenues towards synthesis and applications of amino acid derived heterocycles
Do you wish to request the book?
New avenues towards synthesis and applications of amino acid derived heterocycles
Please be aware that the book you have requested cannot be checked out. If you would like to checkout this book, you can reserve another copy
We have requested the book for you!
Your request is successful and it will be processed during the Library working hours. Please check the status of your request in My Requests.
Oops! Something went wrong.
Looks like we were not able to place your request. Kindly try again later.
Dissertation
New avenues towards synthesis and applications of amino acid derived heterocycles
2003
Overview
This dissertation is divided into five sections. The main focus of this dissertation is on development of new methods for transforming amino alcohols into various synthons. The major part of the work is devoted to Rh(II) catalyzed C-H insertion reactions and their application towards the formation of γ-lactams and isoquinolones. The introductory chapter sheds light on conversion of amino alcohols into various heterocycles. This section further focuses on various methods to form g-lactams and isoquinolones and the advantages and disadvantages with the existing methods. The second chapter of the thesis discusses the development of β-aminobromides. A mild and efficient method is developed for bromination of amino alcohols leading to the formation of rearranged amino bromides. These bromides are converted to original form without any stereochemical leakage upon treatment with oxygen and nitrogen nucleophiles. The reaction mechanism leading to the rearrangement and the effect of neighboring group is discussed in detail. The third chapter is devoted to selective protection of amino group of an amino alcohol as a dithiocarbamate. Despite plethora reactions involving amino alcohols, a very fundamental reaction involving selective protection of amino group is largely ignored. A chemoselective protocol involving an amino alcohol, carbon disulfide, and an alkyl halide in presence of cesium carbonate and TBAI leading to the formation of dithiocarbamate is developed. The reaction is short, simple and devoid of any side products. The fourth chapter deals with regioselective and stereoselective formation of γ-lactams. This methodology is based on Rh(II) C-H insertion of α-diazo α-(phenysulfonyl) acetamide leading to the formation of desired products in favorable ratios. The stereoelectronic effects leading to the desired product are discussed. This methodology was then applied towards the synthesis of Rolipram and Baclofen. Final chapter deals with formal C-H insertion of chiral aryl glycine derived α-diazo α-(phenysulfonyl) acetamides to give rise to chiral isoquinolones as a diastereomer. The mechanism leading to the formation of product is discussed.
