90470-67-0Relevant articles and documents
Photochemical synthesis of acetals utilizing Schreiner's thiourea as the catalyst
Kokotos, Christoforos G.,Nikitas, Nikolaos F.,Spiliopoulou, Nikoleta
supporting information, p. 3539 - 3545 (2020/06/25)
Acetalization of aldehydes is an area of great importance in Organic Chemistry for both synthetic and biological puproses. Herein, we report a mild, inexpensive and green photochemical protocol, where Schreiner's thiourea (N,N′-bis[3,5-bis(trifluoromethyl)-phenyl]-thiourea) is utilized as the catalyst and cheap household lamps as the light source. A variety of aromatic and aliphatic aldehydes were converted into acetals in good to high yields (23 examples, 36-96% yield) and an example of the synthesis of a cyclic acetal is provided. The reaction mechanism was also studied.
Photo-organocatalytic synthesis of acetals from aldehydes
Nikitas, Nikolaos F.,Triandafillidi, Ierasia,Kokotos, Christoforos G.
supporting information, p. 669 - 674 (2019/02/14)
A mild and green photo-organocatalytic protocol for the highly efficient acetalization of aldehydes has been developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied.
Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates
Li, Jiawen,Qian, Bo,Huang, Hanmin
supporting information, p. 7090 - 7094 (2018/11/23)
The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.
Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions
Gagnot, Glwadys,Hervin, Vincent,Coutant, Eloi P.,Desmons, Sarah,Baatallah, Racha,Monnot, Victor,Janin, Yves L.
supporting information, p. 2846 - 2852 (2018/11/27)
We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.
Stepwise construction of discrete heterometallic coordination cages based on self-sorting strategy
Li, Hao,Han, Ying-Feng,Lin, Yue-Jian,Guo, Zi-Wei,Jin, Guo-Xin
supporting information, p. 2982 - 2985 (2014/03/21)
A chelation-directed self-sorting synthesis of a series of cationic heterometallic coordination cages (HCCs) with tunable sizes is described. Two complexation modes were found in the cage-forming process. Metal-anchoring host-guest behavior and size-selective in-cage catalytic activities were found for the HCCs.
Efficient enantioselective synthesis of dihydropyrans using a chiral N, N ′-dioxide as organocatalyst
Feng, Juhua,Fu, Xuan,Chen, Zhenling,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 2640 - 2643 (2013/07/19)
The bifunctional organocatalyst C3 N,N′-dioxide has been successfully applied to the asymmetric cascade Michael/hemiacetalization reaction of α-substituted cyano ketones and β,γ-unsaturated α-ketoesters for the synthesis of multifunctionalized chiral dihydropyrans. The corresponding products were obtained in excellent yields (up to 99%) with high to excellent enantioselectivities (up to 99% ee).
Metal organic frameworks as solid acid catalysts for acetalization of aldehydes with methanol
Dhakshinamoorthy, Amarajothi,Alvaro, Mercedes,Garcia, Hermenegildo
scheme or table, p. 3022 - 3030 (2011/02/24)
Room temperature acetalization of aldehydes with methanol has been carried out using metal organic frameworks (MOFs) as solid heterogeneous catalysts. Of the MOFs tested, a copper-containing MOF [Cu3(BTC)2] (BTC=1,3,5-benzenetricarboxylate) showed better catalytic activity than an iron-containing MOF [Fe(BTC)] and an aluminium containing MOF [Al 2(BDC)3] (BDC=1,4-benzenedicarboxylate). The protocol was validated for a series of aromatic and aliphatic aldehydes and used to protect various aldehydes into commercially important acetals in good yields without the need of water removal. In addition, the reusability and heterogeneity of this catalytic system was demonstrated. The structural stability of MOF was further studied by characterization with powder X-ray diffraction, Brunauer-Emmett- Teller surface area measurements and Fourier-transformed infrared spectroscopic analysis of a deactivated catalyst used to convert a large amount of benzaldehyde. The performance of copper MOF as acetalization catalyst compares favourably with those of other conventional homogeneous and heterogeneous catalysts such as zinc chloride, zeolite and clay. Copyright
Secondary amines and use in pharmaceutical compositions
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, (2008/06/13)
A compound of formula (I): STR1 or a pharmaceutically acceptable salt, ester or amide thereof, in which: W is an optionally substituted phenyl group of the formula STR2 wherein R1 is hydrogen or fluorine, R2 is hydrogen, C1-6 alkyl, halogen or trifluoromethyl; or W is a phenoxymethyl or benzofuran-2-yl group; R3 is C1-12 alkyl or phenyl C1-6 alkyl; A is hydrogen or methyl, X is carboxy, --Z--CO2 H, --Z--OH, T--Z--CO2 H, --Z--NR4 R5, --T--Y--OM, --T--Y--NR4 R5, or --T--R6, in the para- or meta-position with respect to the --(CH2)n group, wherein R4 and R5 are each hydrogen or C1-6 alkyl, R6 is C1-6 alkyl, T is 0, S, --NH or --N--R7, in which R7 is C1-6 alkyl Z is C1-10 straight or branched alkylene optionally containing a carbon-carbon double bond; Y is C2-10 straight or branched alkylene, provided that the hetero atoms in --T--Y--OM and --T--Y--NR4 R5 are separated by at least two carbon atoms, M is hydrogen, C1-6 alkyl or phenyl, and n is 1 or 2, is useful for obesity or hyperglycaemia.
