38228-27-2Relevant academic research and scientific papers
Toward an asymmetric synthesis of the dimeric pyranonaphthoquinone antibiotic crisamicin A
Brimble, Margaret A.,Hassan, Najmah P. S.,Naysmith, Briar J.,Sperry, Jonathan
, p. 7169 - 7178 (2014/08/18)
A full account of our efforts toward an asymmetric synthesis of crisamicin A are presented. The key steps include a Hauser-Kraus annulation of a cyanophthalide with a chiral enone-lactone, a stereoselective cyclization-reduction to install the pyran unit, and a Suzuki homocoupling to forge the key biaryl bond. This work has culminated in the asymmetric synthesis of a dimer bearing the complete carbon skeleton of the dimeric pyranonaphthoquinone natural product crisamicin A.
Ketopyrroles useful as ligands in organic iridium compositions
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Page/Page column 36, (2008/06/13)
The present invention provides novel ketopyrroles having structure XXIV wherein R2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C3-C40 aromatic radical, a C1-C50 aliphatic radical, or a C3-C40 cyclcoaliphatic radical; “a” is an integer from 0 to 3; and X1 and X2 are independently at each occurrence a bromine atom, a hydroxy group, or the group OR10, and wherein the group R10 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C3-C40 aromatic radical, a C1-C50 aliphatic radical, or a C3-C40 cyclcoaliphatic radical. Ketopyrroles XXIV are useful ligands for the preparation of Type (1) and Type (2) organic iridium compositions. In one aspect, the present invention provides deuterated analogs of XXIV. Organic iridium compositions are useful in the preparation optoelectronic devices, such as OLED devices and photovoltaic devices exhibiting enhanced performance characteristics.
Process for preparing isocoumarins
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, (2008/06/13)
The present invention provides a process from preparing isocoumarin-3-yl derivatives comprising reacting a homophthalic anhydride derivative with a carbonyl compound, wherein the carbonyl group is substituted with an acyl activating group, in the presence of a reaction medium comprising a solvent and a base. The invention also encompasses a process for the preparation of homophthalate esters useful in the preparation of homophthalic anhydride reactants as well as an integrated process wherein the twp reactions are carried out sequentially to afford the desired isocoumarin derivative.
Formal synthesis of angiogenesis inhibitor NM-3
Bauta, William E.,Lovett, Dennis P.,Cantrell Jr., William R.,Burke, Brian D.
, p. 5967 - 5973 (2007/10/03)
We report the formal synthesis of angiogenesis inhibitor NM-3 (1) in six steps from either of the 2,4-dimethoxyhalobenzenes 13a,b or 3,5-dimethoxychlorobenzene (13c). The first key reaction is the regiospecific alkylation/rearrangement between the aryne derived from 13a-c with sodium diethylmalonate in THF to produce diester 11, which after hydrolysis and cyclization affords homophthalic anhydride 3. The second is the reaction of anhydride 3 with either ethyl 2-methylmalonate (28a), in the presence of 1,1′-carbonyldiimidazole, or ethyl-2-methylmalonyl chloride (28b) under basic conditions to afford key isocoumarin 27. The conversion of 27 constitutes a formal synthesis of NM-3.
Synthesis of arylspiroketals related to the papulacandins via generation of phthalide oxycarbenium ions
Brimble, Margaret A.,Caprio, Vittorio,Johnston, Andrew D.,Sidford, Matthew
, p. 855 - 862 (2007/10/03)
The nucleophilic addition of allylstannanes to oxycarbenium ions generated from phthalide acetate has been studied. The optimum conditions involve the use of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 °C. Hydroboration of the allylated products followed by oxidative cyclization provides an efficient synthesis of arylspiroketals which are closely related to the papulacandins.
Butyrophenone analogues in the carbazole series as potential atypical antipsychotics: Synthesis and determination of affinities at D2, 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors
Masaguer, Christian F.,Ravina, Enrique,Fontenla, Jose Angel,Brea, Jose,Tristan, Helena,Loza, Maria Isabel
, p. 83 - 95 (2007/10/03)
We describe practical and efficient routes for synthesis of 2- aminomethyl-1,2,3,9-tetrahydro-4H-carbazol-4-ones using the Fischer indole synthesis or palladium-catalysed cyclization methodologies, as well as their affinities for D2, 5-HT(2A) and 5-HT(2C) receptors, and their activity at the 5-HT(2B) receptor. The most active compounds, 4b (QF 2003B) and 4c (QF 2004B), with a pK(i) (5-HT(2A)/D2) ratio of 1.28 show a potential antipsychotic profile according to Meltzer's classification. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
Butyrophenone analogues in the carbazole series: Synthesis and determination of affinities at D2 and 5-HT(2A) receptors
Masaguer, Christian F.,Formoso, Emilio,Ravina, Enrique,Tristan, Helena,Loza, M. Isabel,Rivas, Emilia,Fontenla, Jose Angel
, p. 3571 - 3576 (2007/10/03)
We describe a practical and efficient route for synthesis of 2- aminomethyl-1,2,3,9-tetrahydro-4H-carbazol-4-ones using an effective Fisher indole methodology. The most active compounds, 4b (QF 2003B) and 4c (QF 2004B), with pKi (5-HT(2A)/D2) r
A practical and efficient route for synthesis of 6-aminomethyl-4-oxo- 4,5,6,7-tetrahydroindoles as new CNS agent precursors
Masaguer, Christian F.,Ravina, Enrique
, p. 5171 - 5174 (2007/10/03)
Starting from 2,5-dimethoxybenzoic acid we described a practical and efficient route for synthesis of 6-aminomethyl-4-oxotetrahydroindoles with good to acceptable overall yields of 50-30%.
