Exploration of the synthetic utility of substituted 1,3-amino alcohols and allylamines for generating biodynamic agents

Abstract

The aim of the construction of diverse molecular architectures, required to serve mankind in a variety of ways, is guided by the transformation of a fundamental framework via efficient complexity-generating reactions. Strategies involved in any such venture should be simple, practical, scalable and economical. These prerequisites motivate the organic chemists to explore the potential of simple synthetic intermediates, incorporating flexibility and functionalities, to reach different structural targets. Owing to the propensity to deliver multifunctional products suitable for synthetic tailoring, the MBH reaction has achieved remarkable success in synthetic organic chemistry. Amongst a variety of synthons efficiently afforded from the MBH adducts, allylamines and 1,3-amino alcohols are considered to be of great value since they have been exemplified to be versatile source to an array of important structural motifs. This endeavour incorporates the studies related to the chemical transformations of these two intermediates essentially for the synthesis of azaheterocycles. The first chapter contains a review of the literature showcasing the synthetic strategies employed to obtain 5-, 6- and 7-membered aza-heterocycles from differently substituted allylamines. In the end of the chapter a rationale for performing the present work has been included. The second chapter comprises of the studies carried out for the construction of aza-heterocycles from the primary allylamines derived from the MBH adducts. The synthetic potential of the secondary allylamines and 1,3-amino alcohols for affording nitrogen-heterocycles is presented in the third chapter. The results related to the investigation of reactivity of different pyrazolecarbaldehydes towards MBH reaction are included in the fourth chapter. This chapter also includes the studies related to transformation of the aforementioned MBH adducts to pyrazole-annulated systems via cross coupling reactions. The work on hybrid antimalarials containing the allylamines or 1,3-amino alcohols on the quinoline or quinazoline core has been described in the fifth chapter. The results related to the biological screening of several compounds generated during the present endeavour are presented at the end of the respective chapter. Perspectives drawn from the present work and the literature appearing during the period of accomplishment of this work are compiled at last. Most of the novel observations made during the present work were published which are listed at the end. All the chapters have separate compound numbering in Arabic and bibliography.