67201-30-3Relevant academic research and scientific papers
Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition
Kelly, James M.,Leeper, Finian J.
supporting information; experimental part, p. 819 - 821 (2012/03/10)
The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic α,β-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles.
A new one-pot synthetic approach to the highly functionalized (Z)-2-(buta-1,3-dienyl)phenols and 2-methyl-2H-chromenes: Use of amine, ruthenium and base-catalysis
Ramachary, Dhevalapally B.,Narayana, Vidadala V.,Ramakumar, Kinthada
supporting information; experimental part, p. 3907 - 3911 (2009/04/07)
A practical and simple one-pot multi-catalysis process for the synthesis of highly substituted benzo[b]oxepines 5, (Z)-2-(buta-1,3-dienyl)phenols 6 and 2-methyl-2H-chromenes 7 from simple starting materials was achieved for the first time through ring-closing metathesis/base-induced ring opening/[1,7]-sigmatropic hydrogen shift reactions. The synthesis of privileged (Z)-2-(buta-1,3-dienyl)phenols 6 via base-induced ring opening of highly functionalized benzo[b]oxepines 5 is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Aminodeoxychorismate synthase inhibitors from one-bead one-compound combinatorial libraries: "Staged" inhibitor design
Dixon, Seth,Ziebart, Kristin T.,He, Ze,Jeddeloh, Melissa,Yoo, Choong Leol,Wang, Xiaobing,Lehman, Alan,Lam, Kit S.,Toney, Michael D.,Kurth, Mark J.
, p. 7413 - 7426 (2007/10/03)
4-Amino-4-deoxychorismate synthase (ADCS) catalyzes the first step in the conversion of chorismate into p-aminobenzoate, which is incorporated into folic acid. We aim to discover compounds that inhibit ADCS and serve as leads for a new class of antimicrobial compounds. This report presents (1) synthesis of a mass-tag encoded library based on a "staged" design, (2) massively parallel fluorescence-based on-bead screening, (3) rapid structural identification of hits, and (4) full kinetic analysis of ADCS. All inhibitors are competitive against chorismate and Mg2+. The most potent ADCS inhibitor identified has a Ki of 360 μM. We show that the combinatorial diversity elements add substantial binding affinity by interacting with residues outside of but proximal to the active site. The methods presented here constitute a paradigm for inhibitor discovery through active site targeting, enabled by rapid library synthesis, facile massively parallel screening, and straightforward hit identification.
Synthesis of 4-aminocyclohex-1-enecarboxylates from Danishefsky's diene
Quirante,Vila,Bonjoch
, p. 1971 - 1974 (2007/10/03)
An efficient BF3·Et2O mediated conversion of Diels-Alder adduct 1 of Danishefsky's diene and methyl acrylate yielded cyclohexenones 2 and 3. Subsequent reductive amination with several amines using NaBH(OAc)3 in acetic acid medium gave 4-alkylaminocyclohex-1-enecarboxylate derivatives (4a-e) in a concise form.
An improved synthesis of 4-methylene-2-cyclohexen-1-one
Jung,Rayle
, p. 197 - 203 (2007/10/02)
An improved synthesis of 4-methylene-2-cyclohexen-1-one (1) is described, which involves four steps from commercially available starting materials and proceeds in 65-75% overall yield.
Simple Synthesis and the Diels-Alder Reaction of 3-(p-Tolylthio)-2-(trimethylsilyloxy)-1,3-butadiene
Kosugi, Hiroshi,Hoshino, Kunihide,Uda, Hisashi
, p. 1577 - 1578 (2007/10/02)
The reaction of 3-(p-tolylsulfinyl)-2-butanone with trimethylsilyl trifluoromethanesulfonate in the presence of diisopropylethylamine gave 3-(p-tolylthio)-2-(trimethylsilyloxy)-1,3-butadiene (2) quantitatively.The Diels-Alder reactions of 2 and the relate
The Diels-Alder Route to Allylsilanes from 1-Trimethylsilylbutadienes
Carter, Martin J.,Fleming, Ian,Percival, Alan
, p. 2415 - 2434 (2007/10/02)
The synthesis and Diels-Alder reactions of 1-trimethylsilylbutadiene (3) and its 3-methyl (17), 3-trimethylsilyloxy (20), 4-methyl (4), and 4-trimethylsilyl (6) derivatives are reported.The silyl group reduces somewhat the rate of the Diels-Alder reactions, and has, if anything, a small 'ortho'-directing effect on the regioselectivity in the reactions of (3) with methyl acylate, methyl propiolate, citraconic anhydride, and 2,6-dimethylbenzoquinone.The other substituent in the dienes (17), (20), and (4) is therefore the major influence on the regioselectivity in the reactions of these dienes with methyl acrylate and methyl propiolate.The products of the Diels-Alder reactions of (3), (17), and (4) are allylsilanes, which undergo clean protodesilylation with acid, and, with the acid and ester derived from the maleic anhydride adduct of (3), undergo epoxidation and sulphenylation reactions giving an allyl alcohol (33) and an allyl sulphide (37), respectively.The adducts from (20) can be hydrolysed to β-silylketones, which can be converted into enones by bromination. 1-Pentamethyldisilylbutadiene (15) is no more reactive and no more regioselective than (3).The 'ortho'-adduct (42) from the reaction of (3) and methyl propiolate aromatises with DDQ to give methyl m-trimethylsilylbenzoate (53) in high yield, in a reaction involving rearrangement of the silyl group, even though a direct dehydrogenation is an available pathway.
