Synthesis of New Heterocyclic Compounds Using Lawesson Reagent

Abstract

Lawesson reagent 1 reacts with Mannich bases of β-naphthol 2 and 8-hydroxyquinoline 4 to give oxthiaphosphinine-3-sulfide derivatives 3 and 5, respectively. Reaction of 1 with benzaldehyde in the presence of trialkyl phosphite yields 1,3,5,2-trithiaphosphinane-2-sulfide derivative 8 and, in the presence of ethyl acrylate, affords 2,4,6-triphenyl-1,3,5-trithiane 9. A mechanism is proposed to explain the formation of adduct 3.

The Utility of Carbon Disulphide and Lawesson's Reagent for Synthesis of Different Fused Heterocycles for Antimicrobial Evaluation

“…Heterocyclic compounds containing sulfur, phosphorus, and nitrogen have maintained the interest of researchers through decades of historical development of organic synthesis . On the other hand, carbon disulphide and Lawesson's reagent (LR) have been developed as powerful and versatile reagents in organic synthesis . Continuation to our previous work for using these reagents to synthesize different bioactive heterocycles , we explain in this report the reaction of carbon disulphide and LR with hexahydroquinolines 1a , pyrazolopyranes, and pyrazolopyridines 5a , 5b , 5c , 5d .…”

2-(4-Methoxyphenyl)-4H-1,3,2-benzoxathiaphosphinine 2-sulfide

“…Lawesson's reagent is widely used for transformation of a carbonyl functional group into a thiocarbonyl, see: Ozturk et al (2007). Lawesson's reagent reacts with 1,2-naphthoquinone-1-methide precursors to give 1H-naphtho[1,2-e]-[1,3,2]oxathiaphosphinine 2-sulfide derivatives, which are of interest as herbicides, see: El-Kateb & El-Rahman (2006); El-Kateb et al (1991); Maigali et al (2009). For conformational calculations, see: Cremer & Pople (1975); Zefirov et al (1990); Zotov et al (1997).…”

“…Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2010); based on expressions derived by Clark & Reid (1995)] T min = 0.499, T max = 0.816 27233 measured reflections 4926 independent reflections 4175 reflections with I > 2(I) R int = 0.051 It was shown that Lawesson's reagent reacts with 1,2-naphthoquinone-1-methide precursors to give 1H-naphtho [1,2-e] [1,3,2]oxathiaphosphinine 2-sulfide derivatives which are interesting as herbicides (El-Kateb & El-Rahman, 2006;El-Kateb et al, 1991;Maigali et al, 2009). However, preparation of 4H-1,3,2-benzoxathiaphosphinine 2-sulfides from salicylic alcohols was not described in literature.…”

Reaction of Lawesson's reagent with Mannich base hydrochlorides: synthesis of novel 4H-1,3,2-oxathiaphosphorine-2-sulfide derivatives

“…[5][6][7][8][9][10][11] These heterocycles are an important class of compounds in the medicinal chemistry with interesting biological properties including antimicrobial, antifungal and antitumor activities. [12][13][14] In the last few years, it was shown that the reaction of LR with α, β-unsaturated carbonyl compounds [12,[15][16][17] or phenolic Mannich bases [18,19] can lead to 4H-1,3,2-oxathiaphosphorine derivatives. The scope of these reactions is, however, limited and only a *Corresponding author.…”