20176-08-3Relevant academic research and scientific papers
Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H-Abstraction by Azide Radical
Shee, Maniklal,Shah, Sk. Sheriff,Singh, N. D. Pradeep
supporting information, p. 14070 - 14074 (2020/10/12)
This report presents the visible-light-assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O2. Organic photoredox catalyst, 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene), induces single electron transfer (SET) from azide N3? and generates azide radical N3?.The photogenerated N3? abstracts H atom from α-C?H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN3) in situ. This reaction subsequently forms azido alcohol intermediate that transforms into nitrile with the assistance of triflic acid (Br?nsted acid). A range of alcohols and methyl arenes successfully underwent cyanation at room temperature with good to excellent yields and showed good functional group tolerance.
Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO
Fang, Wan-Yin,Qin, Hua-Li
, p. 5803 - 5812 (2019/05/14)
A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.
Selective synthesis of benzo[4,5]imidazo[2,1-a]isoquinolines via copper-catalyzed tandem annulation of alkynylbenzonitriles with 2-Iodoanilines
Liu, Xiaodong,Deng, Guobo,Liang, Yun
, p. 2844 - 2847 (2018/06/18)
An efficient copper-catalyzed cascade cyclization reaction for selectively synthesizing a variety of benzo[4,5]imidazo[2,1-a]isoquinoline derivatives has been developed. The reaction features the formation of three different C–N bonds in sequence. In the
Rapid synthesis and zebrafish evaluation of a phenanthridine-based small molecule library
Donaldson, Lauren R.,Wallace, Stephen,Haigh, David,Patton, E. Elizabeth,Hulme, Alison N.
supporting information; experimental part, p. 2233 - 2239 (2011/04/27)
A Heck cyclisation approach is described for the rapid synthesis of a library of natural product-like small molecules, based on the phenanthridine core. The synthesis of a range of substituted benzylamine building blocks and their incorporation into the library is reported, together with a highly selective cis-dihydroxylation protocol that enables access to the target compounds in an efficient manner. Biological evaluation of the library using zebrafish phenotyping has led to the discovery of compound 20c, a novel inhibitor of early-stage zebrafish embryo development.
SRN1 SYNTHESES OF BIS(PHENYLTHIO)- AND DICYANO-NAPHTHALENES VIA DIAZOSULFIDES
Novi, M.,Garbarino, G.,Petrillo, G.,Dell'Erba, C.
, p. 2205 - 2212 (2007/10/02)
The reactions of bromonaphthalenediazonium tetrafluoroborates (6a,b and 11a,b) with sodium benzenethiolate in DMSO give, through the preliminary formation of the corresponding diazosulfides (7a,b and 12a,b) bis(phenylthio)naphthalenes (8a,b and 13a,b) deriving from substitution of both the diazo group and the bromine.Isolated diazosulfides (7a,b and 12a,b) likewise furnish satisfactory yields of dinitriles (9a,b and 14a,b) by reaction with excess tetrabutylammonium cyanide in DMSO under photostimulation by a sunlamp.The intervention of an SRN1 process accounting for the formation of the disubstitution products is postulated.
