128408-02-6Relevant academic research and scientific papers
Metal-free domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes: A facile access to oxybis(2-aryltetrahydrofuran) derivatives
Banerjee, Prabal,Dey, Raghunath,Rajput, Shruti
, (2020/03/13)
In this work, we have demonstrated a metal-free transformation of cyclopropane carbaldehydes to oxybis(2-aryltetrahydrofuran) derivatives via a domino Cloke-Wilson rearrangement-hydration-dimerization sequence. Commercially inexpensive p-toluene sulfonic acid (PTSA) was used as a Br?nsted acid catalyst, and reactions were conducted in an open-flask. Detection of reaction intermediates were carried to get an insight into the reaction pathway.
Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine
Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh
supporting information, p. 6535 - 6550 (2020/06/09)
A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.
Exploitation of Cyclopropane Carbaldehydes to Prins Cyclization: Quick Access to (E)-Hexahydrooxonine and Octahydrocyclopenta[ b]pyran
Kumar, Pankaj,Dey, Raghunath,Banerjee, Prabal
supporting information, p. 5163 - 5166 (2018/09/13)
A single-step TiX4-mediated Prins-type cyclization of cyclopropane carbaldehydes with 3-buten-1-ol for the highly stereoselective construction of relatively strained (E)-hexahydrooxonines is reported. Switching the alcohol to 3-butyn-1-ol prompted a similar route, augmented by another cyclization within a nine-membered ring to afford a bicyclized product (4,4-dihalo-5-aryloctahydrocyclopenta[b]pyran). Easy transformation of the resulting geminal dihalide to a vinyl halide and a ketone further supplemented the substance of this approach.
Dual Ligand-Enabled Nondirected C?H Olefination of Arenes
Chen, Hao,Wedi, Philipp,Meyer, Tim,Tavakoli, Ghazal,van Gemmeren, Manuel
supporting information, p. 2497 - 2501 (2018/02/06)
The application of the Pd-catalyzed oxidative C?H olefination of arenes, also known as the Fujiwara–Moritani reaction, has traditionally been limited by the requirement for directing groups on the substrate or the need to use the arene in large excess, ty
Tandem oxidation–Wittig reaction using nanocrystalline barium manganate (BaMnO4); an improved one-pot protocol
Gholinejad, Mohammad,Firouzabadi, Habib,Bahrami, Maedeh,Nájera, Carmen
supporting information, p. 3773 - 3775 (2016/07/26)
A one-pot, tandem oxidation–Wittig procedure has been developed in which the reacting components are generated in situ from alcohols, triphenyl phosphine, and ethyl bromoacetate using barium manganate as a mild oxidizing agent without the addition of an external base.
N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley-Griffith (TPAP) tandem oxidation-Wittig reactions
Read, Christopher D. G.,Moore, Peter W.,Williams, Craig M.
, p. 4537 - 4540 (2015/09/15)
N,N,N′,N′-Tetramethylethylenediamine dioxide (TMEDAO2) was explored as a more atom economical co-oxidant for the Ley-Griffith oxidation of alcohols to aldehydes. TMEDAO2 was found to selectivity oxidise benzylic and allylic alcohols in comparable yields to that of the standard Ley-Griffith co-oxidant (NMO). Importantly TMEDAO2 facilitated tandem Ley-Griffith-Wittig reactions with stabilised ylides, in good to excellent yields, without the requirement of anhydrous conditions.
CANNABINOID RECEPTOR MODULATOR
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Page/Page column 66-67, (2008/06/13)
A cannabinoid receptor modulator containing a compound represented by Formula (I0) wherein, X is an oxygen atom, etc., R° is an optionally substituted acylamino group, ring A0 is a benzene ring which may further have a substituent in addition to R°, and ring B is an optionally substituted 5-membered heterocycle, or a salt thereof or a prodrug thereof.
PROMOTERS FOR THE PROLIFERATION AND DIFFERENTIATION OF STEM CELLS AND/OR NEURON PRECURSOR CELLS
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, (2008/06/13)
An agent for promoting the proliferation or differentiation of a stem cell and/or neural progenitor cell, comprising a compound represented by Formula: wherein each of R1 and R2 is H, a hydrocarbon group or a heterocyclic group, or taken together with the adjacent carbon atom to form a ring, R3 is H, a hydrocarbon group or a heterocyclic group, W is a group represented by Formula: wherein Ring A is an optionally substituted benzene ring, Ring B is an optionally substituted 5- to 7-membered nitrogen-containing heterocyclic ring, R4 is an acyl group having an aliphatic hydrocarbon group, which is substituted by an aromatic group and may have a further substitutent, or aromatic group, R5 is H, C1-6 alkyl or acyl, R4c is an aromatic group, an aliphatic hydrocarbon group or acyl, and X is O or S; Y is O, S or NH, Ring C is an optionally substituted benzene ring, or a salt or prodrug thereof is provided.
Benzofuran derivatives, their production and use
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, (2008/06/13)
Compounds represented by the formula: wherein R1 and R2 are hydrogen atom, a hydrocarbon group or a heterocyclic group, or R1 and R2 may form, together with the adjacent carbon atom, a 3- to 8-membered homocyclic or heterocyclic ring, W indicates (i) a group represented by the formula: wherein ring B indicates a 5- to 7-membered ring, or (ii) a group represented by the formula: wherein R4 indicates (1) an aliphatic hydrocarbon group, which may be substituted with an aromatic group, or (2) an acyl group containing an aromatic group, R5 is hydrogen atom, a C1-6 alkyl, or an acyl group, provided that, when W is Wa, R3 is hydrogen atom, a hydrocarbon group or a heterocyclic group, when W is Wb, R3 indicates a C6-14 aryl group, or salts thereof or prodrugs thereof have an excellent action to inhibit neurodegeneration and the like as well as an excellent brain penetrability and are low in the toxicity, thereby being useful as prophylactic or therapeutic drugs for nerve degenerative diseases and the like.
Electrochemical vinylation of aryl and vinyl halides with acrylate esters catalyzed by cobalt bromide
Gomes, Paulo,Gosmini, Corinne,Nédélec, Jean-Yves,Périchon, Jacques
, p. 5901 - 5903 (2007/10/03)
A consumable anode process permits the electrochemical Heck reaction between aromatic or vinylic halides and acrylate esters using cobalt bromide as catalyst associated with bipyridine as ligand in a mixture of acetonitrile/triethylamine/pyridine as solvent.
