N-Propargylamines: versatile building blocks in the construction of thiazole cores

Abstract

Thiazoles and their hydrogenated analogues are not only key structural units in a wide variety of natural products but they also constitute important building blocks in medicinal chemistry. Therefore, the synthesis of these compounds using new protocols is always interesting. It is well known that N-propargylamines can undergo a number of cyclization reactions to produce various nitrogen-containing heterocycles. In this review, we highlight the most important developments on the synthesis of thiazole and its derivatives starting from N-propargylamines. This review will be helpful in the development of improved methods for the synthesis of natural and biologically important compounds.

Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity

“…Thiazole derivatives containing nitrogen and sulphur atoms are among the most important pharmacophore groups in drug research studies 1 and it is known that many drugs [1][2][3] and natural products 4 such as Abafungin, Famotidin, Meloxicam and Ritonavir contain a thiazole ring in their structures. [1][2][3][4] Thiazoles are present in a wide range of pharmacologically active compounds exhibiting antibacterial, [5][6][7][8] antimycobacterial, [9][10][11] antifungal, [5][6][7][8] anticancer [12][13][14] and antiviral 15,16 activity.…”

“…[1][2][3][4] Thiazoles are present in a wide range of pharmacologically active compounds exhibiting antibacterial, [5][6][7][8] antimycobacterial, [9][10][11] antifungal, [5][6][7][8] anticancer [12][13][14] and antiviral 15,16 activity. Furthermore, thiazole derivatives are useful as chemosensors 17 and fluorescent sensors.…”

KA2‐Coupling Reaction Catalyzed by Semi‐Heterogeneous Magnetically Graphene Oxide Supported Copper Catalyst under Microwave Condition

“…Propargylamines, as high‐value building blocks for many bioactive compounds and several therapeutic drugs, have received widespread attention, ranging from the academic research to industrial application . Therefore, synthesis of this type of compounds has attracted considerable attention from bio‐organic and pharmaceutical chemists for many years . Propargylamines have traditionally been prepared by nucleophilic attack of organometallic reagents, such as Grignard reagent and lithium acetylide on imines or their derivatives .…”

“…[1][2][3] Therefore, synthesis of this type of compounds has attracted considerable attention from bio-organic and pharmaceutical chemists for many years. [4][5][6][7] Propargylamines have traditionally been prepared by nucleophilic attack of organometallic reagents, such as Grignard reagent and lithium acetylide on imines or their derivatives. [8][9][10] However, both reagents were present in stoichiometric amounts and the reactions must be performed under anaerobic and anhydrous conditions.…”

Synthesis and structure-physicochemical properties relationship of thiophene-substituted bis(5,4-d)thiazoles

“…Since the thiazoles are generally known as key structural units in a wide variety of natural products (i.e. abafungin, tiazofurin) (Arshadi et al 2017) the fused bis (5,4-d)thiazoles have been initially screened as inhibitors of central nervous system and antibacterial agents. The high toxicity (LD50 ≥ 0.5 g/Kg) associated with most of pattern TzTz derivatives when tested as CNS depressants, and unsufficient antibacterial activity against various strains of bacteria have excluded thiazolo [5,4-d]thiazoles suitable for further biological applications (Ketcham and Mah 1971).…”