58644-55-6Relevant academic research and scientific papers
Isocyanide 2.0
Ahmadian-Moghaddam, Maryam,D?mling, Alexander,Patil, Pravin
supporting information, p. 6902 - 6911 (2020/11/09)
The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is
Formation of Imidazopyridines by the Phase Transfer Catalyzed Reaction of α-(Aminomethyl)pyridines with CHCl3 and Alkaline Hydroxide
Langry, Kevin C.
, p. 2400 - 2404 (2007/10/02)
The reaction of chloroform with 2-(aminomethyl)pyridine (1) under basic phase-transfer catalysis affords the highly fluorescent imidazopyridine (2) in 25percent isolated yield.Despite the formation of considerable tarry residue, GC-MS indicates that the volatile fraction of the reaction is simple and consists of 2 and two minor components identified as N-(2-pyridylmethyl)formamide (6) and (2-pyridylmethyl)isonitrile (7).The basic phase transfer catalyzed reaction of chloroform with a series of α-(aminomethyl)azanaphthalenes was found to be general and yield the corresponding annulated imidazo derivatives in comparable yields.Despite product yields in the 25percent range, GC of the reaction mixtures indicates that the volatile fractions generally consist of residual starting aminomethyl compound, the imidazo product, and a minor amount of the (α-azanaphthylmethyl)formamide.However, 3-(aminomethyl)isoquinoline (18) failed to provide any of the expected imidazoisoquinoline (19).The failure to detect 19 was investigated.
