Synthesis of 1-trimethylsilyl-2-arylcyclohexenes: a new class of anionic synthons

Synthesis of-4-((4-trimethylsilyl-1H-1,2,3-triazol-1-yl)methyl)-2H-chromen-2-ones: A novel class of heteroaryl anionic synthon

“…[7] Our laboratory deals with the synthesis and reactions of organosilyl-based reagents. [8] In this piece of work, we report for the first instance of time, the synthesis of some novel conjugate heterocyclic scaffolds: the substituted-4-((4-trimethylsilyl-1H-1,2,3-triazol-1-yl) methyl)-2H-chromen-2-ones. The molecules, we expect, would serve as precursors for Scheme 1.…”

A highly efficient synthesis of 1-trimethylsilyl-2-arylcyclopentenes using two consecutive stages of aqueous and anhydrous reactions

“…In further extension of our previous work of the preparation of the 1-trimethylsilyl-2-arylcyclohexenes, 34 the 1-chloro-2-arylcyclopentenes 3a-k obtained through the Suzuki cross-coupling reaction under aqueous microwave conditions, were next subjected to the Wurtz-Fittig cross-coupling reaction to obtain the novel aryl substituted cyclic vinylsilanes 4a-k. Individually refluxing 3a-k with chlorotrimethylsilane and sodium in dry ether solvent afforded the products 4a-k in 62-82% yields (Table 1).…”

“…Table 1.Optimized yields of 1-chloro-2-arylcyclopentenes 3a-k and 1-trimethylsilyl-2-arylcyclopentenes 4a-k We postulate the mechanism for the formation of the five-membered anionic synthons 4a-k from 3a-k to traverse the mechanistic pathway as reported by us earlier. 34 In this article, we would wish to report that in our experience over the years, it is found that the synthesis of the six-membered cyclic vinylsilanes is most favorable and requires less reaction time. 34 In comparison, the synthesis of other medium sized rings, including the five membered rings 4a-k, requires more time and the overall yields are comparatively lesser.…”

“…34 In this article, we would wish to report that in our experience over the years, it is found that the synthesis of the six-membered cyclic vinylsilanes is most favorable and requires less reaction time. 34 In comparison, the synthesis of other medium sized rings, including the five membered rings 4a-k, requires more time and the overall yields are comparatively lesser. We reason that due to ring strain, the isolated yields of the products 4a-k, have been reduced and the time for formation increased.…”

“…In continuation of our previous work, 34 we now wish to report the microwave assisted sequential regiospecific conversion of 1-bromo-2-chlorocyclopentene (1) with eleven arylboronic acids 2a-k to 1-chloro-2arylcyclopentenes 3a-k, under aqueous conditions employing the Suzuki coupling reaction and their subsequent transformation into the vinylsilanes: 1-trimethylsilyl-2-arylcyclopentenes 4a-k as depicted in Scheme 1, employing the Wurtz-Fittig coupling reaction. The first stage employs aqueous reaction conditions, whereas the second stage involves total anhydrous conditions and metallic sodium in ether solvent.…”