- A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives
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A versatile synthetic procedure is described to prepare the benzimidazole-fused 1,2,4-thiadiazoles 2a-c via a methanesulfonyl chloride initiated multistep cyclization involving the intramolecular reaction of an in-situ generated carbodiimide with a thiour
- Samanta, Debabrata,Rana, Anup,Bats, Jan W.,Schmittel, Michael
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- Influence of Anion-Binding Schreiner's Thiourea on DMAP Salts: Synergistic Catalysis toward the Stereoselective Dehydrative Glycosylation from 2-Deoxyhemiacetals
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Amines are used as additives to facilitate or increase the host-guest chemistry between the thiourea and the anions of Bronsted acids. However, we here demonstrate, for the first time, the synergistic effect of the combination of DMAP/HCl/Schreiner's thio
- Ghosh, Titli,Mukherji, Ananya,Kancharla, Pavan K.
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p. 1253 - 1261
(2021/01/14)
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- Click mechanochemistry: Quantitative synthesis of "ready to use" chiral organocatalysts by efficient two-fold thiourea coupling to vicinal diamines
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Mechanochemical methods of neat grinding and liquid-assisted grinding have been applied to the synthesis of mono- and bis(thiourea)s by using the click coupling of aromatic and aliphatic diamines with aromatic isothiocyanates. The ability to modify the re
- Strukil, Vjekoslav,Igrc, Marina D.,Eckert-Maksic, Mirjana,Friscic, Tomislav
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supporting information; experimental part
p. 8464 - 8473
(2012/09/05)
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- Desymmetrisation of aromatic diamines and synthesis of non-symmetrical thiourea derivatives by click-mechanochemistry
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ortho- and para-Phenylenediamines were desymmetrised and quantitatively transformed into mono- and bis-(thio)ureas or mixed thiourea-ureas through a one-pot mechanochemical click reaction sequence; mechanochemical desymmetrisation proceeds quantitatively
- Strukil, Vjekoslav,Margetic, Davor,Igrc, Marina D.,Eckert-Maksic, Mirjana,Friscic, Tomislav
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supporting information
p. 9705 - 9707
(2012/10/29)
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- Dual hydrogen-bond/enamine catalysis enables a direct enantioselective three-component domino reaction
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It takes two to tango: A dual catalyst system, composed of a highly enantioselective enamine catalyst and a multiple-hydrogen-bond catalyst, enabled the chemoselective union of two aldehydes and a nitromethane unit with near-perfect enantioselectivities, excellent diastereoselectivities, and high yields under neutral conditions (see scheme). Copyright
- Rahaman, Hasibur,Madarasz, Udam,Papai, Imre,Pihko, Petri M.
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supporting information; experimental part
p. 6123 - 6127
(2011/08/05)
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- One-pot synthesis of five and six membered N, O, S-heterocycles using a ditribromide reagent
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In a one-pot procedure, bromine less brominating reagent 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been utilized as an efficient desulfurizing agent for the construction of a library of heterocycles containing N, O, and S starting from aryl/alkyl isothiocyanates. In this approach, aryl/alkyl isothiocyanate reacts with o-phenylenediamine (o-PD), o-aminophenol, and o-aminothiophenol to form their monothiourea which on desulfurization with EDPBT led to the formation of corresponding 2-aminobenzimidazoles, 2-aminobenzoxazoles, and 2-aminobenzothiazoles, respectively. An interesting regioselectivity was observed for unsymmetrical thiourea having a naphthyl moiety on the one side and an ortho amino or an ortho hydroxy phenyl group on the other side giving a completely different product which is mainly dependent on the nature of the nucleophiles (-OH or -NH 2). Further, the bis-thioureas resulted from the aliphatic 1,2-diamine with 2 equiv of aryl isothiocyanates on treatment with EDPBT gave imidazolidenecarbothioamides, whereas bis-thioureas resulted from aromatic 1,2-diamine yielded benzimidazoles with concurrent expulsion of an isothiocyanate unit. This method is simple and applied to various substrates which are amenable to bromination that reveals the desulfurizing ability of EDPBT predominating over its brominating ability. Finally, the spent reagent EDPDB can be recovered, regenerated, and reused without any loss of activity.
- Yella, Ramesh,Patel, Bhisma K.
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experimental part
p. 754 - 763
(2010/11/03)
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- Thermolysis of symmetrical dithiobiurea and thioureidoethylthiourea derivatives
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Microwave and thermal heterocyclization of N,N′-disubstituted hydrazinecarbothioamide 1a,b and substituted thioureidoethylthioureas 2a-c as well as 1-phenyl-3[2-(3-phenylthio-ureido)phenyl]-thiourea 6 are reported.
- Hassan, Alaa A.,Mourad, Aboul-Fetouh E.,El-Shaieb, Kamal M.,Abou-Zied, Ashraf H.,Doepp, Dietrich
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p. 535 - 541
(2007/10/03)
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