The tethered Biginelli condensation in natural product synthesis

Abstract

This review describes the development of the tethered Biginelli condensation and its application to the total synthesis of structurally complex, bioactive guanidine alkaloids.

Ionic liquid-functionalized SBA-15 mesoporous material: efficient heterogeneous catalyst in versatile organic reactions

“…This is due to their pharmacological and therapeutic properties such as antibacterial and antihypertensive activity in addition to their behaving as calcium channel blockers, a-1a-antagonists and neuropeptides Y (NPY) antagonists. [27] The Biginelli reaction is one of the multicomponent reactions (MCRs) and most important procedures for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones. In general, Biginelli reactions are simple one-pot, but low-yielding, condensations of β-dicarbonyl compounds with aldehydes and urea.…”

Biginelli reaction for synthesis of novel trifluoromethyl derivatives of bis(tetrahydropyrimidinone)benzenes

“…In this context, the one-pot cyclocondensation of acetoacetic esters with aromatic aldehydes and (thio)urea, known as Biginelli reaction [5], has been one of the most well studied MCRs in recent years. The reaction affords formation of dihydropyrimidine derivatives as an important substructure of many synthetic [6][7][8][9] and natural compounds [10][11][12][13] that exhibit diverse pharmacological and therapeutic properties [14][15][16][17] such as antiviral, antibacterial, anti-inflammatory, and antitumor activities. In addition, several dihydropyrimidine containing alkaloids are isolated from marine sources which possess bilological and anti-HIV properties [18,19].…”

NH3(CH2)6NH3SiF6 catalyzed highly efficient synthesis of benzimidazoles, benzoxazoles, benzothiazoles, quinoxalines and pyrimidin-2-ones/thiones

“…The reusability of the catalyst was also investigated on the models reactions for the synthesis of compounds 3a, 8a and 10a. In order to compare the efficiency of our catalyst with respect to the other catalysts [9][10][11][12]18,[22][23][24][25][26][41][42] reported for the synthesis of benzimidazole, benzothiazole, benzoxazole, 3,4-dihydro pyrimidin-2-thione, 3,4-dihydro pyrimidin-2-one and quinoxaline, the results are tabulated in Table 8. As it is clear from and benzothiazoles 5 in high yields (90-98%, Table 3).…”

“…The 3,4-dihydropyrimidin-2-ones/thiones, which have been synthesized by a multicomponent reaction, are very important heterocyclic motif in the realm of natural and synthetic organic chemistry due to possessing different biological and pharmacological activities, such as antibacterial [18], antitumor [19] and antiviral [20] properties.…”