116815-00-0Relevant articles and documents
N,N′-Dibutylbarbituric acid as an acceptor moiety in push-pull chromophores
Klikar, Milan,Bures, Filip,Pytela, Oldrich,Mikysek, Tomas,Padelkova, Zdenka,Barsella, Alberto,Dorkenoo, Kokou,Achelle, Sylvain
, p. 4230 - 4240 (2013)
Twelve novel D-π-A chromophores with the N,N′-dibutylbarbituric acid acceptor, the N,N-dimethylamino donor and a systematically extended π-linker were synthesized. The extent of intramolecular charge-transfer, structure-property relationships and nonlinear optical properties were further investigated by X-ray analysis, electrochemistry, UV/Vis absorption spectra, calculations and EFISH experiments.
Two-Step Synthesis of (Z)-3-Aryl-5-(arylmethylidene)butenolides by an Ivanov Reaction/Silver(I)-Catalyzed Lactonization/In Situ Dehydration Sequence
Hermann, David,Arican, Deniz,Brückner, Reinhard
, p. 326 - 352 (2016/12/24)
A stereoselective synthesis of the title compounds was developed. Hexane- and amine-free THF solutions of α-lithiated lithium arylacetates ('arylacetic acid dianions') were aldol-added to 3-arylpropynals. This gave 2,5-diaryl-3-hydroxypent-4-ynoic acids with up to a 72:28 preference for the anti-diastereomer (27 examples + 1 exception). When treated with Ag2CO3 (1-20 mol%) in DMF at room temperature for 2.5 days, the respective mixtures underwent regio- and stereoselective lactonizations followed by an in situ dehydration. Thereby 3-aryl-5-(arylmethylidene)butenolides were obtained with a Z-configuration of the oxygenated C=C bond. Their overall yields ranged from 46% to 83% (1 exception: 28%). Three 3-aryl-5-(arylmethylidene)butenolides contained a C-Br and/or a C-I bond. They allowed a subsequent Pd-catalyzed C-C coupling, which furnished follow-up butenolides.
Efficient one-pot preparation of methylthio arylbutadiynes by double elimination protocol
Su, Qiong,Yan, Hong,Gao, Shi-Chao,Xie, De-Xun,Cai, Qing-Yun,Shao, Guang,Peng, Zhi-Hong,An, De-Lie
supporting information, p. 2648 - 2655 (2013/07/26)
A novel and efficient method for preparation of methylthio arylbutadiynes (Ar-C≡C-C≡C-SCH3) was described, and a series of compounds have been expediently obtained by the one-pot protocol starting from methylthiomethyl phenyl sulfone (MP-S) and arylpropargyl aldehydes. The mechanism was discussed on the basis of trapping and characterization of key intermediates. The results from experiments indicated that the reaction involved the initial nucleophilic addition of MP-S to arylpropargyl aldehydes to produce an intermediate carrying two leaving groups and subsequent double elimination reactions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.