4873-09-0Relevant articles and documents
Preparation process of triallyl isocyanurate (by machine translation)
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Paragraph 0010; 0013-0030, (2020/07/02)
The preparation process is characterized in that allyl alcohol is used as a raw material, allyl alcohol and p-toluenesulfonyl chloride are prepared into allyl tosylate through an acid binding agent; and the prepared allyl tosylate is reacted with sodium cyanate, a phase transfer catalyst and a polar solvent to obtain triallyl isocyanurate. To the preparation method, allyl alcohol is adopted as the raw material, atmospheric pollution is reduced, the reaction rate is higher, the yield of triallyl isocyanurate is improved, the environment is protected, and the energy-saving and consumption-reducing effect is remarkable. (by machine translation)
Facile synthesis of 1-Alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications
Lakshman, Mahesh K.,Singh, Manish K.,Kumar, Mukesh,Chamala, Raghu Ram,Yedulla, Vijayender R.,Wagner, Domenick,Leung, Evan,Yang, Lijia,Matin, Asha,Ahmad, Sadia
, p. 1919 - 1932 (2014/11/07)
(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4- methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads to 1-alkoxy-1H-benzo- (Bt-OR) and 7-azabenzotriazoles (At-OR). Although BOP undergoes reactions with alcohols to furnish 1-alkoxy-1H-benzotriazoles, Bt-OTs proved to be superior. Both, primary and secondary alcohols undergo reaction under generally mild reaction conditions. Correspondingly, 1-alkoxy-1H-7-azabenzotriazoles were synthesized from At-OTs. Mechanistically, there are three pathways by which these peptide-coupling agents can react with alcohols. From 31P{1H}, [18O]-labeling, and other chemical experiments, phosphonium and tosylate derivatives of alcohols seem to be intermediates. These then react with BtO- and AtO- produced in situ. In order to demonstrate broader utility, this novel reaction has been used to prepare a series of acyclic nucleoside-like compounds. Because BtO- is a nucleofuge, several Bt-OCH2Ar substrates have been evaluated in nucleophilic substitution reactions. Finally, the possible formation of Pd πallyl complexes by departure of BtO- has been queried. Thus, alpha-allylation of three cyclic ketones was evaluated with 1-(cinnamyloxy)-1H-benzo[d][1,2,3]triazole, via in situ formation of pyrrolidine enamines and Pd catalysis.
Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenation
Del Valle, David J.,Krische, Michael J.
supporting information, p. 10986 - 10989 (2013/08/23)
The triene-containing C17-benzene ansamycins trienomycins A and F were prepared in 16 steps (longest linear sequence, LLS) and 28 total steps. The C11-C13 stereotriad was generated via enantioselective Ru-catalyzed alcohol CH syn crotylation followed by chelation-controlled carbonyl dienylation. Enantioselective Rh-catalyzed acetylene-aldehyde reductive coupling mediated by gaseous H2 was used to form a diene that ultimately was subjected to diene-diene ring closing metathesis to form the macrocycle. The present approach is 14 steps shorter (LLS) than the prior syntheses of trienomycins A and F, and 8 steps shorter than any prior synthesis of a triene-containing C17-benzene ansamycin.