Reactions of p‐quinone monoimines with lawesson reagent and phosphorus pentasulfide

Abstract

2, 3,2,awesson reagent (LR)

Action of Lawesson's reagent on substituted 2-amino-1,4-naphthoquinones: Novel synthesis of benzodiphenoquinone-bis-1,3,2-thiazaphospholine-2-sulfide derivatives

“…Moreover, the present study clearly shows that Lawesson's reagent reacts with 2-amino-1,4-naphthoquinones 2a-d in a manner rather different from that already known of quinones [4][5][6]. Also, this discovery, which represents a novel route to 3, is a supplement to the expanded utility of reagent 1 for the new synthesis of bisthiazophospholine derivatives 3a-d.…”

“…With p-quinones and p-quinonediimines, it gives 1,3,2-benzoxathiaphosphol-5-ol-2-sulfides and 1,3,2-benzazathiaphosphol-2-sulfides, respectively [4,5]. Moreover, we have reported that Lawesson's reagent 1 reacts with p-quinone monoimines to give the corresponding 1,3,2-benzoxathiaphosphol-2-sulfide and 1,3,2-dithiaphosphol-2-sulfide derivatives [6]. As part of our continuing interest in organophosphorus chemistry [7][8][9][10][11][12], we describe here the reaction of Lawesson's reagent 1 with substituted 2-amino-1,4-naphthoquinones 2a-d (Scheme 1).…”

The reaction of organophosphorus reagents with substituted‐1,3‐diphenylpropanetrione: New synthesis of azaphospholene derivatives

“…Trisdimethylaminophosphine 6a (0.32;0.002 mol) was added dropwise to a solution of compound 5 [1] (0.36 g, 0.01 mol) in dry toluene (30 ml) and the reaction mixture was refluxed for 4 hours. After evaporation of the volatile materials under reduced pressure, the residue was applied to silica gel column chromatography using acetone/ petroleum ether (12:78, v:v) 3 ), and at 7.05-6.65 (m,15H,Ar.). 31 P NMR: δ = +40.89.…”

“…We have reported [1] that trialkyl phosphites (1a-c) react with 2-(phenylimino)-1,3-diphenylpropanedione (2a) and 2-(phenylmethylene)-1,3-diphenylpropane dione (2b) to give the corresponding phosphonate adducts (3a-c) and (4a-c), respectively (Scheme 1). As part of our continuing interest in organophosphorus syntheses [2][3][4][5][6][7][8][9][10], we describe here the reactivity of 1,3-(phenylimino)-3-(ylidenemethylacetate)-1-propanone (5) toward trisdialkylaminophosphines (6a,b) and trialkyl phosphites (1a-c). The purpose of this study was to determine the preferential site of attack by these reagents.…”

Studies on phosphonium ylides XX. The behavior of Wittig reagents toward 1,4‐benzoquinone monoimines

“…During the course of our studies on the behavior of 1,4-benzoquinone monoimines 2 toward organophosphorus compounds [ 1-31, we concluded that alkyl phosphites [1,2], the Lawesson reagent, and phosphorus pentasulfide [3] preferentially attack the carbonyl oxygen of p-quinone monoimines 2 rather than the imino groups. Moreover, we have reported [ 1,2] that N-(methylsulfonyl)-1,4-benzoquinone monoimine 2b behaves toward alkyl phosphites in a different manner than that found for N-(phenylsulfony1)-1 ,Cbenzoquinone monoimine 2a with the same alkyl phosphites.…”