436088-93-6Relevant articles and documents
New growth regulators of corn based on N-mono- and N,N-bis-3-butenyldichloroacetamides
Bubnov, Yu. N.,Spiridonov, Yu. Ya.,Kuznetsov, N. Yu.
, p. 345 - 358 (2018/05/22)
Allylboration of imines, nitriles (including hydrocyanic acid), amides, lactams, aromatic azaheterocycles (pyridines, isoquinoline, and pyrrole) was used to synthesize a series of mono- and bis-3-butenylamines with different structures, which were converted to dichloroacetamides, new analogs of a known safener (herbicide antidote) Dichlormid successfully used in the cultivation of corn throughout the world. Biological tests for the germination of corn seeds showed that most of the dichloroacetamides obtained have growth-stimulating activity, which is mainly directed on the development of the root system. Compounds 2f, trans- and cis-2n, cis-2s, and 2t demonstrated outstanding activity, exceeding from two to three times the stimulating effect of Dichlormid on the developing root system of maize seedlings.
Synthesis of bridged azabicycles from pyridines and pyrrole by a diallylboration - Ring closing metathesis sequence
Kuznetsov, Nikolai Yu.,Khrustalev, Viktor N.,Godovikov, Ivan A.,Bubnov, Yuri N.
, p. 113 - 120 (2007/10/03)
A straightforward method for the preparation of bridged azabicycles by a diallylboration-ring closing metathesis (RCM) sequence was elaborated. The precursors for the metathesis reaction were prepared by reductive irons-diallylation of aromatic heterocycles such as pyridines, isoquinoline and pyrrole with triallylborane and an alcohol. Heating of the irons isomers with one equivalent of triallylborane allowed the corresponding cis isomers - or (in the case of pyrrole) a mixture of cis and trans isomers - to be obtained. Boc protection of the amine function gave the precursor for the RCM reaction with axial orientations of allylic groups. The chemical yields of this stage are very good and the amounts of Grubbs' catalyst required for the reaction do not exceed 2.5 mol-% (first generation cat.) or 3.7 mol-% (second generation cat.). Azabicyclo[4.2.1]nonene, obtained from pyrrole, is a key structural motif of the toxin pinnamine. The structures of cis-1,3-diallyl-1,2,3,4- tetrahydroisoquinoline and azabicyclo[4.3.1]-decadiene were studied by single-crystal X-ray analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.