107367-72-6Relevant academic research and scientific papers
Single-step microwave-mediated synthesis of oxazoles and thiazoles from 3-oxetanone: A synthetic and computational study
Orr, David,Tolfrey, Alexandra,Percy, Jonathan M.,Frieman, Joanna,Harrison, Zo? A.,Campbell-Crawford, Matthew,Patel, Vipulkumar K.
supporting information, p. 9655 - 9662 (2013/07/26)
The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of (hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles. The reactions use a sustainable solvent and only require short reaction times. These are highly competitive methods for the construction of two classes of valuable heteroarenes, which bear a useful locus for further elaboration. Electronic structure calculations have shown that the order of events involves chalcogen atom attack at sp3 carbon and alkyl-oxygen cleavage. The critical role of acid catalysis was shown clearly, and the importance of acid strength was demonstrated. The calculated barriers were also fully consistent with the observed order of thioamide and amide reactivity. Spontaneous ring opening involves a modest degree of C-O cleavage, moderating the extent of strain relief. On the acid-catalysed pathway, C-O cleavage is less extensive still, but proton transfer to the nucleofuge is well advanced with the carboxylic acid catalysts, and essentially complete with methanesulfonic acid. Open sesame: The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of oxazoles and thiazoles. The reactions use a sustainable solvent, require only short reaction times and represent a highly competitive method for the construction of two classes of valuable heteroarenes. Electronic structure calculations have been used to probe a range of potential reaction mechanisms (see figure). Copyright
OXAZOLYL-METHYLETHER DERIVATIVES AS ALX RECEPTOR AGONISTS
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Page/Page column 34-35, (2012/06/30)
The invention relates to oxazolyl-methylether derivatives of formula (I), wherein R1, R2, R3, R4 and R5 are as defined in the description, their preparation and their use as pharmaceutically active co
Heterocyclic compounds, their production and use
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, (2008/06/13)
Heterocyclic compounds represented by the general formula (I) wherein R stands for an optionally substituted aromatic heterocyclic group; X stands for oxygen atom, an optionally oxidated sulfur atom, —C(═O)— or —CH(OH)—; Y stands for CH or N; m denotes an integer of 0 to 10: n denotes an integer of 1 to 5: cyclic group ?stands for an optionally substituted aromatic azole group; and ring A is optionally further substituted, or salts thereof. The compound (I) possesses action of inhibiting tyrosine kinase and useful as antitumor agents.
Application of complex aldol reactions to the total synthesis of phorboxazole B
Evans,Fitch,Smith,Cee
, p. 10033 - 10046 (2007/10/03)
The synthesis of phorboxazole B has been accomplished in 27 linear steps and an overall yield of 12.6%. The absolute stereochemistry of the C4-C12, C33-C38, and C13-C19 fragments was established utilizing catalytic asymmetric aldol methodology, while the absolute stereochemistry of the C20-C32 fragment was derived from an auxiliary-based asymmetric aldol reaction. All remaining chirality was incorporated through internal asymmetric induction, with the exception of the C43 stereocenter which was derived from (R)-trityl glycidol. Key fragment couplings include a stereoselective double stereodifferentiating aldol reaction, a metalated oxazole alkylation, an oxazole-stabilized Wittig olefination, and a chelation-controlled addition of the fully elaborated alkenyl metal side chain.
