- Access to Cyanoimines Enabled by Dual Photoredox/Copper-Catalyzed Cyanation of O-Acyl Oximes
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An efficient strategy for the synthesis of pharmaceutically important and synthetically useful cyanoimines, as well as cyanamides, has been described. This strategy is enabled by dual photoredox/copper-catalyzed cyanation of O-acyl oximes or O-acyl hydroxamides. This state of the art protocol for cyanoimines and cyanamides features readily available starting materials, mild reaction conditions, good functional group tolerance, and operational simplicity. The resultant cyanoimines can be transformed into structurally diverse and functionally important N-containing heterocycles.
- Wei, Ziyan,Yu, Shouyun,Zhang, Ai Hua,Zhang, Hao
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supporting information
p. 7315 - 7320
(2020/10/02)
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- Radical N-cyanation of sulfoximine through acetonitrile C-CN cleavage
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A new strategy for the N-cyanation of sulfoximine via radical process has been developed, leading to the desired products in moderate to excellent yields with good functional group tolerance. This procedure provided an alternative pathway to C-CN bond act
- Hu, Weiming,Teng, Fan,Peng, Haibo,Yu, Jintao,Sun, Song,Cheng, Jiang,Shao, Ying
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supporting information
p. 7056 - 7058
(2015/11/27)
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- Copper-catalyzed N-cyanation of sulfoximines by AIBN
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The direct copper-catalyzed N-cyanation of sulfoximines was achieved by using AIBN as a safe cyanide source. It represents a simple and environmentally benign procedure for the construction of the N-CN bond. Furthermore, some sec-amines can also be tolera
- Teng, Fan,Yu, Jin-Tao,Zhou, Zhou,Chu, Haoke,Cheng, Jiang
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p. 2822 - 2826
(2015/03/18)
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- Alkylidenecyanamidium Salts. α-Bromination of Carbodiimides
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Carbodiimides (15) of type H-C-N=C=N-R react with N-bromosuccinimide (NBS) to afford unstable alkylidenecyanamidium bromides (18) which undergo von Braun elimination of R-Br giving the alkylidenecyanamides 19 if R is a tertiary alkyl group.Reaction of car
- Joachims, Johannes C.,Rahman, Mohammed Abdur
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p. 502 - 516
(2007/10/02)
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- Formation and Thermal Cleavage Reactions of the Cycloadduct of 9,10-Dimethylanthracene and Nitrosyl Cyanide
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Nitrosyl cyanide and 9,10-dimethylanthracene (DMA) (2) reacted at -25 deg C to form the crystallyne cycloadduct, 9,10-dihydro-9,10-(N-cyanoepoxyimino)-9,10-dimethylanthracene (1).The adduct (1) decomposed in the presence of the conjugated diene thebaine (3), to form DMA(2) and the adduct (4) of nitrosyl cyanide and thebaine.First-order kinetics, k = 6.9E-5 s-1, were observed for the release of DMA in benzene at 40 deg C, consistent with slow dissociation of the adduct (1) followed by rapid capture of nitrosyl cyanide by thebain.A similar first-order rate, k = 6.8E-5 s-1, was observed for the reaction of the adduct (1) and triphenylphosphine (2 mol equiv.) under the same conditions, the products being DMA, triphenylphosphine oxide, and triphenylphosphine N-cyanoimide (5).The reactions of nitrosyl cyanide, generated thermally from the adduct (1), were studied with a range of dienes.The conjugated dienes, N-cyanomethyl-N-northebaine (3; NCH2CN replacing NMe), trans,trans-1,4-diphenylbuta-1,3-diene (6; R=H), and ergosteryl acetate (11) all gave the expected cycloadducts (3,6-dihydro-2H-1,2-oxazines).Norbornane gave the tetracyclic adduct (10) arising from 1,4-conjugate addition of nitrosyl cyanide.The reactions of the adduct (1) with tetraphenylcyclopentadienone (14), 1,3-diphenylisobenzofuran (18), 2-methyl-1,3-diphenylisoindole (23), diazofluorene (24), and diphenyldiazomethane all took a more complex course leading in each case to the formation of an N-cyano-ketimine (alkylidene-cyanamide)
- Horsewood, Peter,Kirby, Gordon W.,Sharma, Ram Prakash,Sweeny, James
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p. 1802 - 1806
(2007/10/02)
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- Substituted cyanamidic compounds
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Substituted cyanamidic compounds as exemplified by N-(diphenylmethylidene)cyanamide may be prepared by reacting nitrogen-containing compounds having the formula: STR1 in which R1 and R2 are selected from the group consisting of hydrogen, aryl, alkyl possessing from 1 to about 30 carbon atoms, cycloalkyl possessing from about 5 to about 12 carbon atoms in the ring, alkyl-substituted cycloalkyl, aryl-substituted cycloalkyl, alkaryl and aralkyl radicals and R3 is selected from the group consisting of hydrogen, alkyl possessing from 1 to about 30 carbon atoms, aryl, cycloalkyl possessing from 5 to about 12 carbon atoms in the ring, alkyl-substituted cycloalkyl, aryl-substituted cycloalkyl and bicycloalkyl radicals with cyanamide and a compound selected from the group consisting of an acid-acting compound, an alkyl halide and an alkyl sulfate.
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