80095-85-8Relevant academic research and scientific papers
Reactivity and diastereoselectivity of Michael additions of amines to achiral α,β-unsaturated thioamides
So?nicki, Jacek G,Jagodziński, Tadeusz S,Hansen, Poul Erik
, p. 8705 - 8718 (2007/10/03)
Heterocyclic, aliphatic amines add to acyclic and cyclic α,β-unsaturated thioamides yielding β-amino-functionalized derivatives. In the case of cyclic acceptors, the formation of both kinetic and thermodynamically controlled products is observed. Tailorin
Thionation of ω-hydroxy amides with Lawesson's reagent: Synthesis of thioenamides and sulfur-containing heterocycles
Nishio, Takehiko,Sekiguchi, Hiroshi
, p. 5017 - 5026 (2007/10/03)
The thionation of ω-hydroxy amides with Lawesson's reagent [LR: 2,4- bis(p-methoxyphenyl)-1,3,2,4-dithiaphosphetane-2,4-disulfide] is described. The treatment of 3-hydroxy amides 1 with LR exclusively gave thioenamides 2 in fair yields. The treatment of 4-hydroxy amides 5 with LR yielded sulfur- containing heterocycles such as tetrahydrothiophene-2-imines 6 and tetrahydrothiophene-2-thione 7a through cyclization of intermediates, 4- mercapto amides 8. The 5-hydroxy amides 13 also reacted with LR to afford tetrahydrothiopyrane-2-thione 14 as the the sole product.
Sulfur-containing heterocycles derived by the reaction of hydroxy-amides and Lawesson's reagent
Nishio, Takehiko
, p. 6113 - 6116 (2007/10/02)
A simple one-pot reaction between hydroxy-amides (1), located 1,3- or 1,4- to each other, and Lawesson's reagent (LR) gives sulfur-containing heterocycles such as tetrahydrothiophene-2-imines (4), tetrahydrothiophene-2-thione (5) and tetrahydrothiopyran-2
Studies on Organophosphorus Compounds. XXXVIII. Synthesis of 2,3-Unsaturated O-Alkyl Thioesters, 2,3-Unsaturated Thioamides and Tetrahydro-2H-1,3,2-thiazaphosphorin-4-one 2-Sulfides
Scheibye, S.,Lawesson, S.-O.,Roemming, C.
, p. 239 - 246 (2007/10/02)
Ethyl 2-butenoate (ethyl crotonate), ethyl 3-phenyl-2-propenoate (ethyl cinnamate), methyl2-cyano-3-phenyl-2-propenoate, and ethyl 2-cyano-3,3-diphenyl-2-propenoate, react with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, 1, at 140 deg C in xylene under formation of the corresponding O-alkyl thioesters.N-Unsubstituted, N-substituted, and N,N-disubstituted 3-phenyl-2-propenamides (cinnamamides) as well as N,N-disubstituted 2-butenamides (crotonamides) give the corresponding thioamides when treated with 1 in toluene at 60 deg C. 2-Propenamide, 2-butenamide, and 3-methyl-2-butenamide give, however, 2H-1,3,2-thiazaphosphorin-4-ones, 10-12, after recation with 1 in HMPA at 60 deg C.The 6-methyl derivative, 11, was separated in the cis and trans forms and spectroscopic data of these isomers and X-ray crystallographic data of trans-11 are given.The 2H-1,3,2-thiazaphosphorin-4-one, 10, is readily transformed into the corresponding 4-thione by reaction with 1 at 90 deg C in toluene.
