Design Synthesis and Biological Evaluation of Substituted 2_Amino_1_3_Thiazines and Trans N_ Substituted Pyrrolidines Bearing 1_2_4_Triazoles

Abstract

Most important disciplines of organic chemistry are synthesis of heterocyclic compounds. In the realm of medical chemistry and pharmaceutical chemistry, heterocyclic compounds with N and O atoms play an important function. Heterocyclic compound containing Nitrogen, Oxygen and Sulphur heteroatoms such as thiazine and triazoles exhibits numerous properties and have wide applications in pharmaceutical industrial sector. Furthermore, they have grown in significance not only in the industry but also in the growth of human civilization. The main objective of thesis work is to design and synthesise novel heterocyclic compounds through readily available chemicals. The thesis has been divided into four important chapters as shown below: newline newlineCHAPTER 1: newline newlineThis chapter reviews the literature on the synthesis and pharmacological applications of a few fused Nitrogen, Oxygen, and Sulphur heterocycles, particularly thiazines and 1,2,4-triazoles, which are relevant to this study. newline newlineCHAPTER 2: newline newlineThe second chapter describes the literature survey review and synthesis of 2-amino substituted 1,3-thiazine derivatives. newline newlineA novel series of substituted 2-amino-1,3-thiazines were synthesized as amides 9a-i, carbamates 9j-m, sulphonamides 9n-o and urea derivatives 9p-q by treating the compound 7 with acid chlorides 8a-i, chloroformates 8j-m, sulfonyl chlorides 8n-o and isocyanates 8p-q respectively. newlineBased on pharmacological importance, the researcher has designed new hybrid molecules having privileged pharmacophores. The synthesis consists of following steps. newline newlinea) Intermediate 6-methyl-4-phenyl-6H-1,3-thiazin-2-amine 7 was prepared by using cyclization of 3-chloro-1-phenylbutan-1-one with thiourea 6 in ethanol at reflux for 8 hr. newline newlineb) Finally, the target thiazine compounds 9a-9q were prepared by coupling of amine 7 with various acid chlorides 8a-8i, chloroformates 8j-8m, sulfonyl chlorides 8n-8o, and phenyl isocyanates 8p-8q in presence of DIPEA in CH2Cl2 at room temperature for 2 hr as illustrated in below scheme. newline newline