119072-55-8Relevant articles and documents
Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3
Li, Jing,Okuda, Yasuhiro,Zhao, Jiaji,Mori, Seiji,Nishihara, Yasushi
, p. 5220 - 5223 (2014)
An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate α-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.
Filippou, A. C.
, p. 1285 - 1292 (1989)
Tandem reaction strategy of the Passerini/Wittig reaction based on the in situ capture of isocyanides: One-pot synthesis of heterocycles
Liu, Ming-Guo,Liu, Na,Xu, Wen-Heng,Wang, Long
, p. 2748 - 2754 (2019)
This paper reports the tandem reaction strategy of the Passerini/Wittig reaction based on the in situ capture of isocyanides. According to this strategy, plenty of isocyanides have been synthesized, which is immediately used for the tandem reaction of Passerini/Wittig reaction in one pot. Compared to the previous work, this strategy avoids the separation, purification, and storage of isocyanides, which prominently solves the problems of isocyanide-based multicomponent reaction such as: (a) The environmentally unfriendly (strong foul odor), (a) the labile of Isocyanides, (c) high toxicity of isocyanides. In the meantime, in order to expand the application scope of our strategy, 1H-isochromenes and 3H-2-benzoxepin-1-ones have also been synthesized, which undergoes four-step transformations in one-pot. In addition, a relatively credible reaction mechanism has also been proposed, based on a series of control experiments. Furthermore, preliminary testing was performed on biological activity of some obtained compounds; These results showed that the synthesized compounds exhibited certain activity over P. digitatum and P. italicum. 2019 Elsevier Science. All rights reserved.
Band et al.
, p. 7380 (1977)
Quast,Schaefer
, p. 1057 (1977)
Facile Synthesis of Cyanide and Isocyanides from CO
Grimme, Stefan,Kooij, Bastiaan,Lin, Jack H.,Qu, Zheng-Wang,Stephan, Douglas W.,Wang, Tongtong,Xu, Maotong
supporting information, p. 16965 - 16969 (2021/06/28)
The reaction of K[N(SiMe3)2] with 13CO proceeds in C6D6 or THF affording K13CN and O(SiMe3)2 under mild conditions as confirmed by crystallographic characterization of K(18-crown-6)CN. Similarly reaction of the alkali metal amides, M[N(SiR3)R′] (M=Li, K; R=Ph, Me; R′=alkyl, aryl) provides the corresponding 13C labeled isocyanide RN13C and MOSiR3, generally in high yields. In some instances, the use of the sterically bulky Ph3Si-substituent is required to preclude 1,2-silyl migration affording the silylcarbamoyl salt M[Me3SiC(O)NR′]. These reactions have been used to obtain 19 examples of 13C labelled isocyanides, and several examples of gram scale reactions are reported. The mechanism of the reactions is probed via reliable DFT calculations.
Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides
Liu, Na,Chao, Fei,Liu, Ming-Guo,Huang, Nian-Yu,Zou, Kun,Wang, Long
, p. 2366 - 2371 (2019/05/16)
This paper reports the tandem reaction strategy of the Passerini/Staudinger/aza-Wittig reaction based on the in situ capture of isocyanides. According to this strategy, isocyanides are synthesized in situ and immediately work as the substrate for the Passerini reaction and postmodification tandem reaction in one pot. In addition, two types of new compounds, 5-oxo-3,5-dihydrobenzo[e][1,4]oxazepines and 6-oxo-5,6-dihydro-2H-1,4-oxazines, were synthesized using the tandem reaction strategy that includes five-step transformations in one pot.
