- α-(Aryithio)imidoyl Radicals: [3 + 2] Radical Annulation of Aryl Isothiocyanates with 2-Cyano-Substituted Aryl Radicals
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A novel cascade radical reaction is described involving aryl isothiocyanates and 2-cyanoaryl radicals. The mechanism entails the formation of an α-(arylthio)imidoyl radical, a 5-exo-dig cyclization onto a cyano group, and a final 6-membered ring closure o
- Leardini, Rino,Nanni, Daniele,Pareschi, Patrizia,Tundo, Antonio,Zanardi, Giuseppe
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- Synthesis of Isothiocyanates and Unsymmetrical Thioureas with the Bench-Stable Solid Reagent (Me4N)SCF3
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A highly efficient, selective, and rapid transformation of primary amines and diamines to isothiocyanates and cyclic thioureas is disclosed. As opposed to established approaches that employ toxic or volatile electrophilic liquids and require reaction control (i.e., slow addition, cooling), this protocol utilizes the bench-stable, solid reagent (Me4N)SCF3 at room temperature. The method is characterized by operational simplicity, high speed, efficiency, high functional group tolerance, and late-stage applicability. The byproducts are solids, allowing isolation of the target compounds by filtration.
- Scattolin, Thomas,Klein, Alexander,Schoenebeck, Franziska
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supporting information
p. 1831 - 1833
(2017/04/11)
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- In situ generation and trapping of thioimidates: An intermolecular tandem reaction to 4-acylimino-4H-3,1-benzothiazines
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The proton-catalyzed transformation of 2-thioureidobenzonitriles to 4-acylimino-4H-3,1-benzothiazines was accomplished by treatment with carboxylic anhydrides, acid chlorides or alkyl chloroformates. The reaction involves a cyclization to 4-imino-3,1-benz
- Steinebach, Christian,Schulz-Fincke, Anna-Christina,Schnakenburg, Gregor,Gütschow, Michael
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p. 15430 - 15440
(2016/02/23)
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- Triazoloquinazolines as a novel class of phosphodiesterase 10A (PDE10A) inhibitors
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Novel triazoloquinazolines have been found as phosphodiesterase 10A (PDE10A) inhibitors. Structure-activity studies improved the initial micromolar potency which was found in the lead compound by a 100-fold identifying 5-(1H-benzoimidazol-2-ylmethylsulfan
- Kehler, Jan,Ritzen, Andreas,Langgard, Morten,Petersen, Sebastian Leth,Farah, Mohamed M.,Bundgaard, Christoffer,Christoffersen, Claus Tornby,Nielsen, Jacob,Kilburn, John Paul
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scheme or table
p. 3738 - 3742
(2011/07/31)
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- The synthesis of 2-cyano-cyanothioformanilides from 2-(4-Chloro-5H-1,2,3- dithiazol-5-ylideneamino)benzonitriles using DBU
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A series of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino) benzonitriles were prepared from the reaction of 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) and the corresponding anthranilonitriles. Reaction of the 1,2,3-dithiazolimines with DBU (3 e
- Michaelidou, Sophia S.,Koutentis, Panayiotis A.
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experimental part
p. 4167 - 4174
(2011/02/27)
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- Vibrational spectroscopic studies and ab initio calculations of 2-cyanophenylisocyanid dichloride
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FT-Raman and FT-IR spectra of 2-cyanophenylisocyanid dichloride were recorded and analyzed. The vibrational frequencies of the title compound have been computed using the Hartree-Fock/6-31G* basis and compared with the experimental values. The
- Varghese, Hema Tresa,Panicker, C. Yohannan,Philip, Daizy,Pazdera, Pavel
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p. 1055 - 1059
(2008/02/06)
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- Synthesis and X-ray characterisation of a new polycondensed heterocycle obtained by a novel Mn(III)-mediated cascade reaction of 2-cyanophenyl isothiocyanate
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2-Cyanophenyl isothiocyanate reacted with Mn(III) acetate in acetic acid or acetonitrile to give fair yields of a new polycondensed heterocycle arising from the joining together of two molecules of the starting isothiocyanate with loss of a CS moiety. The yields were close to 90% when the reaction was carried out in the presence of diethyl malonate. This compound was unambiguously identified by X-ray crystallography. Under the same conditions, 2-(methoxycarbonyl)phenyl isothiocyanate gave a quinazolinimine derivative instead which is likely to arise from cyclisation of an intermediate N,N′-diarylthiourea. The mechanism of formation of the former compound probably involves formation of a N,N′-bis(2-cyanophenyl)thiourea, followed by rearrangement and radical tandem ring closure of the corresponding cyclic imine derivative. This hypothesis is also supported by semiempirical calculations.
- Calestani, Gianluca,Capella, Laura,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Papa, Romina,Zanardi, Giuseppe
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p. 7221 - 7233
(2007/10/03)
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- New syntheses of aryl isothiocyanates
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Primary aromatic amines are readily converted into arylimino-1,2,3-dithiazoles 2 and the derived cyanothioformanilides 6, both of which are rapidly cleaved by ethylmagnesium bromide in hot THF to give the corresponding isothiocyanates. The transformation 2→6→ArNCS can be performed as a 'one-pot' operation. The imines 2 are also converted, more slowly, into the isothiocyanates by sodium hydride in hot THF, via the cyanothioformanilides 6. Conversion of the anilides 6 into isothiocyanates is much faster under microwave irradiation in 2,6-lutidine. Mechanisms are proposed for these reactions.
- Besson, Thierry,Guillard, Jerome,Rees, Charles W.,Thiery, Valerie
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p. 889 - 892
(2007/10/03)
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- New syntheses of aryl isothiocyanates from N-arylimino-1,2,3-dithiazoles
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Treatment of N-arylimino-1,2,3-dithiazoles 2 with ethylmagnesium bromide (2 equiv.) gives the corresponding aryl isothiocyanates 13, providing a very mild two-step conversion of ArNH2 into ArNCS avoiding hazardous reagents; alternatively the iminodithiazoles 2 can be converted into cyanothioformanilides 11 which rapidly give the same isothiocyanates with 1 equiv. of the Grignard reagent.
- Besson, Thierry,Guillard, Jerome,Rees, Charles W.,Therisod, Michel
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p. 881 - 882
(2007/10/03)
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- Reactivity of 3-amino-4-imino-2-thioxo-1,2,3,4-tetrahydroquinazolines and 3-amino-4-imino-2-selenoxo-1,2,3,4-tetrahydroquinazolines
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The preparation of 6-imino-2H,6H-1,3,4-thiadiazino[2,3-b]quinazolines and 6-imino-2H,6H-1,3,4-selenadiazino[2,3-b]quinazolines by condensation of α-haloketones with 3-amino-4-imino-2-thioxo-1,2,3,4-tetrahydroquinazoline and 3-amino-4-imino-2-selenoxo-1,2,
- Pfeiffer,Pazdera,Hetzheim,Mucke
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