Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

• ]azaphosphole 2-oxides 56 by oxidation with mCPBA, while treatment of 1,3-dihydrobenzo[d][1,2]azaphosphole 2-oxides 56 with phosphorus pentasulfide transformed them back to 1,3-dihydrobenzo[d][1,2]azaphosphole 2-sulfides 60. Heating dimethyl 2-aminobenzylphosphonate (61) generated 1-methyl-2-methoxy-1,3

Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols

• Chandra Kant Maurya,
• Avik Mazumder and
• Pradeep Kumar Gupta

Beilstein J. Org. Chem. 2017, 13, 1184–1188, doi:10.3762/bjoc.13.117

• /bjoc.13.117 Abstract In this paper we report an efficient and mild procedure for the conversion of organic thiocyanates to thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. The method avoids the use of expensive and hazardous transition metals and harsh reducing agents, as

• required by reported methods, and provides an attractive alternative to the existing methods for the conversion of organic thiocyanates to thiols. Keywords: dithiocarbamate; phosphorus pentasulfide; thiocyanate; thiol; toluene; Introduction Thiols constitute an important group of sulfur-containing

• -reductive conditions (Scheme 1). Phosphorus pentasulfide (P2S5), a commercially available reagent, has widely been employed in organic synthesis for numerous applications [18]. The synthetic protocol described in this paper makes use of this reagent to provide an efficient and single step procedure for the

A novel method for heterocyclic amide–thioamide transformations

• Walid Fathalla,
• Ibrahim A. I. Ali and
• Pavel Pazdera

Beilstein J. Org. Chem. 2017, 13, 174–181, doi:10.3762/bjoc.13.20

• ; for instance, Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide) [1][2][3], Berzelius reagent [4][5][6] (P4S10), and phosphorus pentasulfide [7] in dry toluene, xylene or pyridine under reflux conditions. A two-step approach for the purpose of thiation of

New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates

• Darren L. Riley,
• Joseph P. Michael and
• Charles B. de Koning

Beilstein J. Org. Chem. 2016, 12, 2609–2613, doi:10.3762/bjoc.12.256

• Carius tube at 250 °C, affording alcohol 5 in 81% yield. The subsequent protection of the primary alcohol as acetate 6 (87% yield), followed by thionation with phosphorus pentasulfide using the Brillon procedure [29] afforded thiolactam 3 in 90% yield. The succeeding Eschenmoser reaction with α

Regioselective synthesis of 7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione derivatives: A new drug-like heterocyclic scaffold

• Nikolay T. Tzvetkov,
• Harald Euler and
• Christa E. Müller

Beilstein J. Org. Chem. 2012, 8, 1584–1593, doi:10.3762/bjoc.8.181

• main challenge in the synthesis of 23–25 was the construction of the 1,2,4-triazine ring. Direct reaction of 13–15 with hydrazine hydrate failed, and only the corresponding hydrazides were formed. Therefore, the C5 carbonyl group of 13–15 was regioselectively thionated with phosphorus pentasulfide in

• phosphorus pentasulfide in dioxane for four hours. As reported in the literature, we observed only the preferred C4 thiocarbonyl product while the thionation of 5-unsubstituted hydantoin yields a mixture of 2- and 4-thionated products, indicating that the 5-dimethyl substitution was responsible for

Sexithiophenes as efficient luminescence quenchers of quantum dots

• Christopher R. Mason,
• Yang Li,
• Paul O’Brien,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

• ) and phosphorus pentasulfide (24.2 g, 54.5 mmol) in 1,4-dioxane (150 mL) was stirred whilst the temperature was raised to 90 °C. This temperature was maintained for 3 h. The mixture was cooled, water (200 mL) was added portionwise (CAUTION! H2S and CO2 evolution) and the suspension was stirred