206271-34-3Relevant academic research and scientific papers
Rhodium-catalysed hydroformylation of N-(2-propenyl)-β-lactams as a key step in the synthesis of functionalised N-[4-(2-oxoazetidin-1-yl)but-1-enyl] acetamides
Dekeukeleire, Stijn,D'Hooghe, Matthias,Mueller, Christian,Vogt, Dieter,De Kimpe, Norbert
, p. 1079 - 1083 (2010)
Biologically relevant functionalised N-[4-(2-oxoazetidin-1-yl)-but-1-enyl] acetamides have been prepared in a two-step approach starting from N-(2-propenyl)-β-lactams, involving initial rhodium-catalysed hydroformylation followed by subjection of the obta
An efficient microwave method for the synthesis of imines
Border, Emily C.,Blair, Victoria L.,Andrews, Philip C.
, p. 844 - 848 (2015/05/20)
A large variety of aryl and heterocyclic chiral and achiral imines can be generated simply, efficiently, and cleanly through the use of microwave irradiation and the use of a small amount of molecular sieve. Reactions are rapid and complete in a matter of minutes, and can be quantitative, reducing significantly the time and amount of solvents used in compound isolation and purification.
Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives
Hardy, Simon,Martin, Stephen F.
, p. 7142 - 7157 (2017/09/12)
A multicomponent, Mannich-type assembly process commencing with commercially available bromobenzaldehydes was sequenced with [3+2] dipolar cycloaddition reactions involving nitrones and azomethine ylides to generate collections of fused, bicyclic scaffolds based on the 2-arylpiperidine subunit. Use of the 4-pentenoyl group, which served both as an activator in the Mannich-type reaction and a readily-cleaved amine protecting group, allowed sub-libraries to be prepared through piperidine N-functionalization and cross-coupling of the aryl bromide. A number of these derivatives displayed biological activities that had not previously been associated with this substructure. Methods were also developed that allowed rapid conversion of these scaffolds to novel, polycyclic dihydroquinazolin-2-ones, 2-imino-1,3-benzothiazinanes, dihydroisoquinolin-3-ones, and bridged tetrahydroquinolines.
Facile and unified approach to skeletally diverse, privileged scaffolds
Sahn, James J.,Su, Justin Y.,Martin, Stephen F.
supporting information; experimental part, p. 2590 - 2593 (2011/07/08)
A novel strategy has been developed to generate a diverse array of privileged scaffolds from readily available tetrahydropyridine precursors that may be prepared by a multicomponent assembly process followed by a ring-closing metathesis. The functionality embedded in these key intermediates enables their facile elaboration into more complex structures of biological relevance by a variety of ring-forming processes and refunctionalizations.
Multicomponent assembly and diversification of novel heterocyclic scaffolds derived from 2-arylpiperidines
Hardy, Simon,Martin, Stephen F.
supporting information; experimental part, p. 3102 - 3105 (2011/08/10)
A collection of structurally diverse, polyheterocyclic scaffolds comprising a 2-arylpiperidine subunit were synthesized using a Mannich-type multicomponent assembly process, followed by appropriately sequenced ring-forming reactions. An improved procedure
Facile syntheses of substituted, conformationally-constrained benzoxazocines and benzazocines via sequential multicomponent assembly and cyclization
Sahn, James J.,Martin, Stephen F.
scheme or table, p. 6855 - 6858 (2012/02/05)
A multicomponent assembly process (MCAP) was utilized to prepare versatile intermediates that are suitably functionalized for subsequent cyclizations via Ullmann and Heck reactions to efficiently construct substituted 2,6-methanobenzo[b][1,5]oxazocines an
Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent
Smith, Catherine J.,Smith, Christopher D.,Nikbin, Nikzad,Ley, Steven V.,Baxendale, Ian R.
supporting information; experimental part, p. 1927 - 1937 (2011/04/21)
Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction and purification flow process was designed, allowing access to amine products in an automated fashion.
Synthesis of diverse heterocyclic scaffolds via tandem additions to imine derivatives and ring-forming reactions
Sunderhaus, James D.,Dockendorff, Chris,Martin, Stephen F.
experimental part, p. 6454 - 6469 (2011/02/26)
A novel strategy has been developed for the efficient syntheses of diverse arrays of heterocyclic compounds. The key elements of the approach comprise a Mannich-type, multicomponent coupling reaction in which functionalized amines, aromatic aldehydes, acy
Microwave-assisted rapid and simplified hydrogenation
Banik, Bimal K.,Barakat, Khaled J.,Wagle, Dilip R.,Manhas, Maghar S.,Bose, Ajay K.
, p. 5746 - 5753 (2007/10/03)
Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 °C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 °C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of β-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters. Cleavage of the β-lactam ring by hydrogenolysis of the N-C4 bond of 4- aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.
