13670-35-4Relevant articles and documents
Morita–Baylis–Hillman-Type [3,3]-Rearrangement: Switching from Z- to E-Selective α-Arylation by New Rearrangement Partners
Zhang, Lei,Bao, Wangzhen,Liang, Yuchen,Pan, Wenjing,Li, Dongyang,Kong, Lichun,Wang, Zhi-Xiang,Peng, Bo
, p. 11414 - 11422 (2021)
α-aryl α,β-unsaturated carbonyls represent an important class of derivatizable synthetic intermediates, however, the synthesis of such compounds still remains a challenge. Recently, we showcased a novel Z-selective α-arylation of α,β-unsaturated nitriles with aryl sulfoxides via [3,3]-rearrangement involving an Morita–Baylis–Hillman (MBH) process. Herein, we demonstrate the feasibility of reversing the stereoselectivity of such MBH-type [3,3]-rearrangement by switching to a new pair of rearrangement partners consisting of aryl iodanes and α,β-unsaturated oxazolines. As a result, the two protocols complement each other in approaching E- or Z-α-aryl α,β-unsaturated carbonyl derivatives. Mechanistic studies reveal a possible reaction pathway and provide an explanation for the opposite stereoselectivities.
Potentiation of the fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida
Stephens, Matthew D.,Yodsanit, Nisakorn,Melander, Christian
supporting information, p. 1952 - 1956 (2016/10/22)
A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida. From the screen a highly potent 2-oxazoline adjuvant was discovered capable of potentiating FR 900098 with a 1000-fold reduction in MIC against the Francisella sub-species F. novicida and F. philomiragia.
Synthesis of cinnamic acid-derived 4,5-dihydrooxazoles
Kronek, Juraj,Nedelcev, Tomas,Mikulec, Marcel,Kleinova, Angela,Luston, Jozef
, p. 1424 - 1432 (2013/07/26)
A range of cinnamic units containing 4,5-dihydrooxazoles was prepared using two different synthetic routes. The first method was based on the transformation of substituted cinnamic or benzoic acids to 2-styryl-4,5- dihydrooxazoles. Several derivatives con
A convenient synthesis of 2-oxazolines and 2-benoxazoles with PPh3-DDQ as the dehydrating reagent
Xu, Quancai,Li, Zhengning,Chen, Huiying
experimental part, p. 925 - 932 (2012/01/03)
2-Oxazolines and 2-benoxazoles were synthesized in high yields from acylamino alcohols and acylaminophenols, respectively, with triphenylphosphine- 2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DDQ) as the dehydrating and activating reagent. The synthesis was accomplished under neutral conditions.
A facile synthesis of 2-oxazolines using a PPh3-DDQ system
Xu, Quancai,Li, Zhengning
experimental part, p. 6838 - 6840 (2010/04/29)
A facile and efficient synthesis of 2-oxazolines from N-(2-hydroxyethyl)amides using a triphenylphosphine-2,3-dichloro-5,6-dicyanobenzoquinone (PPh3-DQQ) system is described. The reaction proceeds under neutral and mild conditions, and excellent yields are obtained.
Convenient one-pot synthesis of 2-oxazolines from carboxylic acids
Hioki, Kazuhito,Takechi, Yumiko,Kimura, Noriyo,Tanaka, Hiroyuki,Kunishima, Munetaka
experimental part, p. 1735 - 1737 (2009/10/10)
Simple one-pot methods for preparation of 2-oxazolines have been developed using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). Treatment of a mixture of carboxylic acids and 2-haloethylammonium salts with DMT-MM in methanol
Diastereoselective dimerisation of alkenylthiazolines: A combined synthetic and computational study
Beutler, Ariane,Davies, Christopher D.,Elliott, Mark C.,Galea, Natasha M.,Long, Matthew S.,Willock, David J.,Wood, John L.
, p. 3791 - 3800 (2007/10/03)
The acylative dimerisation of 2-alkenyl-1,3-thiazolines 1 gives compounds 3 and 8 upon treatment with trichloroacetyl chloride and trifluoroacetic anhydride, respectively. This reaction is completely diastereoselective, in particular giving only a single
