- Palladium-catalyzed carbonylative synthesis of N-cyanobenzamides from aryl iodides/bromides and cyanamide
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A novel and convenient protocol for the synthesis of N-cyanobenzamides starting from readily available aryl halides and cyanamide via palladium-catalyzed aminocarbonylation has been developed. The protocol utilizes Mo(CO)6 as the CO source or CO(gas) and affords the desired N-cyanobenzamides in moderate to good yields.
- Mane, Rajendra S.,Nordeman, Patrik,Odell, Luke R.,Larhed, Mats
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- Ultrasound-Assisted Synthesis of N -Acylcyanamides and N -Acyl-Substituted Imidazolones from Carboxylic Acids by Using Trichloroisocyanuric Acid/Triphenylphosphine
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A convenient ultrasound-assisted one-pot synthesis of N -acylcyanamides starting from readily available carboxylic acids and sodium cyanamide has been developed. Upon activation in the presence of trichloroisocyanuric acid (TCCA) and triphenylphosphine, a range of carboxylic acids was converted into N -acylcyanamides in good to excellent yields within 10 minutes at room temperature without base. Remarkably, N -acyl-substituted imidazolones were readily accessible through guanylation-cyclization of the in situ generated N -acylcyanamides.
- Phakhodee, Wong,Yamano, Dolnapa,Pattarawarapan, Mookda
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supporting information
p. 703 - 707
(2020/04/08)
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- COMPOSITIONS AND METHODS COMPRISING SUBSTITUTED 2-AMINOIMIDAZOLES
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The present invention presents 2-(acylamino)imidazoles with therapeutic activity, including selective activity against cancer cells, and compositions comprising them. Methods of using and preparing the 2-(acylamino)imidazoles are also presented.
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Paragraph 0208; 0211
(2018/10/25)
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- Copper(I)-catalyzed cascade synthesis of 2-arylsulfanyl-arylcyanamides
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We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl- arylcyanamide was the major product obtained via an intramolecular C-S bond formation, associated with C-S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).
- Sahoo, Santosh K.,Jamir, Latonglila,Guin, Srimanta,Patel, Bhisma K.
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experimental part
p. 2538 - 2548
(2010/12/29)
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- Novel two-step, one-pot synthesis of primary acylureas
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A new procedure for the synthesis of primary acylureas from cyanamide and a variety of carboxylic acids is described. Under mild reaction conditions, the products were obtained in good yield from commercially available starting materials.
- Xiao, Zili,Yang, Michael G.,Tebben, Andrew J.,Galella, Michael A.,Weinstein, David S.
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experimental part
p. 5843 - 5844
(2010/11/05)
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- Desulfurization and transformation of isothiocyanates to cyanamides by using sodium bis(trimethylsilyl)amide
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Sodium bis(trimethylsilyl)amide was first used as the desulfurizing agent for the conversion of isothiocyanates to cyanamides in a 'one-flask' reaction. Crown Copyright
- Chen, Chun-Yen,Wong, Fung Fuh,Huang, Jiann-Jyh,Lin, Shao-Kai,Yeh, Mou-Yung
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supporting information; scheme or table
p. 6505 - 6507
(2009/04/06)
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- Sodium bis(trimethylsilyl)amide in the 'one-flask' transformation of isocyanates to cyanamides
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Cyanamides were successfully prepared in a 'one-flask' reaction from isocyanates by use of sodium bis(trimethylsilyl)amide as the deoxygenating agents in THF at room temperature. Georg Thieme Verlag Stuttgart.
- Wong, Fung Fuh,Chen, Chun-Yen,Yeh, Mou-Yung
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p. 559 - 562
(2007/10/03)
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- Synthesis of bis(arylcarbonylamino-1H-benzimidazol-5-yl) ethers
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A procedure has been developed for the synthesis of bis(arylcarbonylamino- 1H-benzimidazol-5-yl) ethers by reaction of the corresponding substituted benzoyl chloride with sodium cyanamide, followed by treatment of the resulting N-cyanobenzamide with 4-(3,4-diaminophenoxy)benzene-1,2-diamine in acid medium. Nauka/Interperiodica 2006.
- Pilyugin,Sapozhnikov,Chikisheva,Kiseleva,Vorob'eva,Klimakova,Sapozhnikova,Kuznetsova
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p. 1327 - 1330
(2008/02/04)
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- Bis-arylsulfonamide derivatives of 2-amino-5(6)-(4-aminophenylthio)benzimidazole
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Three different procedures have been developed for the preparation of bis-arylsulfonamide derivatives of 2-amino-5(6)-(4-aminophenylthio)benzimidazole, and biological activity of the products have been studied.
- Pilyugin,Mikhailyuk,Kosareva
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p. 1782 - 1789
(2007/10/03)
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- Acylated cyanamide composition for treating ethanol ingestion
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Acylated cyanamide compounds useful for ethanol deterrence of the formula RCONHCN, wherein R is a lipophilic acyl group or is derived from an (N-substituted)-alpha-aminoacyl group.
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- Reactions of Trimethylsilyl Azide with Heterocumulenes
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Trimethylsilyl azide (TMSA) reacted with aryl isocyanates to give arylcarbamoyl azides, 1-aryl-5(4H)-tetrazolinones, and / or 1-aryl-4-(arylcarbamoyl)-5(4H)-tetrazolinones, whose yields were dependent on the reaction conditions.The reaction between TMSA and benzoyl or thiobenzoyl isocyanates provides a facile method for the preparation of 5-aryl-3-hydroxy-1,2,4-oxadiazoles or -1,2,4-thiadiazoles, respectively.However, with phenyl or benzoyl isothiocyanate, 1-anilino-1,2,3,4-thiatriazole or benzoylcyanamide was obtained in low yield, respectively.TMSA reacted with carbodiimides to afford the corresponding 5-aminotetrazoles.Tetraphenylsuccinimide, N-(diphenylacetyl)tetraphenylsuccinimide, 1,3-bis(diphenylmethyl)urea, and / or benziloylamide were obtained from the reaction of TMSA with diphenyl ketene.The pathways for the formation of the above products are also described.
- Tsuge, Otohiko,Urano, Satoshi,Oe, Koji
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p. 5130 - 5136
(2007/10/02)
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