181308-92-9Relevant articles and documents
Continuous-flow preparation and use of β-chloro enals using the Vilsmeier reagent
Pellegatti, Laurent,Buchwald, Stephen L.
, p. 1442 - 1448 (2012/10/29)
The Vilsmeier reagent is used in the preparation of a wide variety of heterocycles, such as pyrazoles, via formation of β-chloroacrolein intermediates. However, use of this extremely reactive reagent on large scale requires special precautions to avoid potentially dangerous exotherms. This article describes the safe preparation at room temperature of the Vilsmeier reagent under flow conditions for the formation of β-chloroacroleins and 3-formylchromones, as well as the use of these in multistep, continuous flow processes for the syntheses of β-acrylonitriles and polysubstituted pyrazoles.
The application of vinylogous iminium salt derivatives to a regiocontrolled and efficient relay synthesis of Lukianol A and related marine natural products
Gupton, John T.,Krumpe, Keith E.,Burnham, Bruce S.,Webb, Tammy M.,Shuford, Jordan S.,Sikorski, James A.
, p. 14515 - 14522 (2007/10/03)
Numerous novel pyrrole containing marine natural products have been shown to possess interesting biological properties. These compounds have been the synthetic targets of several research groups and we have previously reported synthetic methods which util
Synthesis and stereochemistry of β-aryl-β-haloacroleins: Useful intermediates for the preparation of (Z) and (E)-2-en-4-ynecarbaldehydes and for the synthesis of rubrolides
Prim, Damien,Fuss, Alexia,Kirsch, Gilbert,Silva, Artur M. S.
, p. 1175 - 1180 (2007/10/03)
The synthesis of α-substituted β-aryl-β-haloacroleins by two different pathways is presented. The determination of their stereochemistry by NOE experiments is reported for the first time. Furthermore, we describe the preparation of 2-en-4-ynecarbaldehydes
Cytotoxicity of substituted alkyl-3,4-bis(4-methoxyphenyl)pyrrole-2- carboxylates in L1210 lymphoid leukemia cells
Burnham,Gupton,Krumpe,Webb,Shuford,Bowers,Warren,Barnes,Hall
, p. 337 - 341 (2007/10/03)
Two alkyl-3,4-bis(4-methoxyphenyl)pyrrole-2-carboxylates proved to be potent cytotoxic agents in the murine L1210 lymphoid leukemia screen. DNA synthesis was preferentially inhibited with the major target of the agents being de novo purine biosynthesis at the regulatory enzyme sites of PRPP- amido transferase and IMP dehydrogenase. Other enzymatic activities which were suppressed by the drugs were DNA polymerase α, RNA polymerases, ribonucleoside reductase and dihydrofolate reductase. The d[NTP] pools, nucleoside kinase and the pyrimidine pathway were not affected by the presence of drugs. The DNA molecule itself was not the target of the agents, i.e. no alkylation of nucleotide bases, intercalation between bases or cross- linking of DNA strands occurred. The agents did cause L1210 DNA fragmentation after 24 h incubation at 100 μM.