146980-79-2Relevant academic research and scientific papers
Iodocarbamation of N-Homopropargyl Carbamates: Mild and Stereoselective Entry to Functionalized Oxazinan-2-ones
Quinodoz, Pierre,Quelhas, Alexandre,Wright, Karen,Drouillat, Bruno,Marrot, Jér?me,Couty, Fran?ois
, p. 2621 - 2626 (2017)
An efficient and general iodocarbamation of benzyl N-homopropargylcarbamates has been developed by using iodine as the electrophilic agent. This regio- and stereoselective cyclization yielded (E)-6-iodomethyleneoxazinan-2-ones, which can be further transformed through palladium cross-coupling reactions followed by hydrogenation to produce 1,3-oxazinan-2-ones.
Synthesis of homopropargylamines from 2-cyanoazetidines
Quinodoz,Wright,Drouillat,David,Marrot,Couty
supporting information, p. 10072 - 10075 (2016/08/15)
2-Cyanoazetidines, easily accessible from β-amino alcohols, undergo ring-cleavage upon reaction with trimethylsilylazide and catalytic amounts of Bu2SnO, to give the corresponding homopropargylamines which are isolated as their N-Boc protected
Enantio- and diastereoselective palladium catalysed arylative and vinylative allene carbocyclisation cascades
Li, Meiling,Hawkins, Alison,Barber, David M.,Bultinck, Patrick,Herrebout, Wouter,Dixon, Darren J.
supporting information, p. 5265 - 5267 (2013/06/27)
The enantioselective synthesis of heavily decorated spirolactams has been accomplished via an arylative or vinylative allene carbocyclisation cascade. Mediated by silver phosphate, a range of allene-linked pro-nucleophiles and aryl or vinyl iodides were reacted in the presence of catalytic Pd(OAc)2 and chiral bis(oxazoline) ligands to afford the spirolactam products in good yields and high enantio- and diastereoselectivities. The Royal Society of Chemistry 2013.
Palladium-catalysed cyclisation of N-alkynyl aminomalonates
Hess, Wilfried,Burton, Jonathan W.
supporting information; experimental part, p. 12303 - 12306 (2011/02/23)
Go around in (hetero)cycles! The palladium-catalysed tandem cyclisation/coupling reaction of alkynyl- and alkenyl-substituted aminomalonates leads to highly functionalised pyrrolidines and piperidines in good yield (see scheme). The reaction allows efficient access to a broad range of synthetically valuable building blocks.
Indenylidene complexes of ruthenium: Optimized synthesis, structure elucidation, and performance as catalysts for Olefin metathesis - Application to the synthesis of the ADE-ring system of nakadomarin A
Fuerstner, Alois,Guth, Oliver,Dueffels, Arno,Seidel, Guenter,Liebl, Monika,Gabor, Barbara,Mynott, Richard
, p. 4811 - 4820 (2007/10/03)
An optimized and large scale adaptable synthesis of the ruthenium phenylindenylidene complex 3 is described which employs commercially available diphenyl propargyl alcohol 5 as a stable and convenient carbene source. Previous ambiguities as to the actual
Synthesis of N-{[4-(2-amino-4(3H)-oxo-5,6,7,8-tetrahydro-(9H)- pyrimido[4,5-b]-azepin-6-yl)methyl]benzoyl}-L-glutamic acid and two of its conformationally-restricted analogs
Read, Mark W.,Miller, Michael L.,Ray, Partha S.
, p. 373 - 392 (2007/10/03)
Synthesis of the titled tetrahydropyrimidoazepine-based folate (6a) is described using a regiospecific γ-alkylation reaction between the dienolate generated from 3-carboethoxy-N-2,4-dimethoxybenzyl-1,5,6,7-tetrahydro-(1H)- azepin-2-one (33) and methyl 4-formylbenzoate, as the key step. The isoxazolinopyrimidoazepine and isoxazolopyrimidoazepine-based folates (7a and 8a respectively) were also prepared (via intramolecular 1,3-dipolar cycloaddition chemistry) as conformationally-restricted analogs of 6a. All three compounds were prepared as potential antitumor agents based on the known, structurally related, antitumor agent 5,10-dideaza-5,6,7,8- tetrahydrofolic acid (DDATHF). Both 7a and 8a were inactive in the human colon carcinoma (GC3c1) cell culture assay. Compound 6a, however, was weakly active (IC50 = 2.0 μM) in the above assay.
