88039-45-6Relevant academic research and scientific papers
Poly(ethyleneglycol) (PEG): A rapid and recyclable reaction medium for the DABCO-catalyzed Baylis-Hillman reaction
Chandrasekhar,Narsihmulu, Ch.,Saritha,Shameem Sultana
, p. 5865 - 5867 (2004)
PEG (400) has been used as a rapid and recyclable reaction medium for the Baylis-Hillman reaction with the conventional basic catalyst DABCO (20mol%) with very good yields of products. Recyclability is achieved with no further addition of DABCO to the rea
Chiral benzomorphan derivative, and preparation method and pharmaceutical application thereof
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Paragraph 0107-0109, (2020/12/08)
The invention belongs to the field of synthetic pharmacochemistry, and relates to a chiral benzomorphan compound of a structure as shown by a general formula shown in the specification and capable ofbeing used as an opium receptor ligand, and application
Silver/palladium relay catalyzed 1,3-dipole annulation/allylation reactions to access fully substituted allyl imidazolidines
Han, Ruiping,Ding, Yue,Jin, Xueke,Li, Er-Qing
supporting information, p. 646 - 649 (2020/02/11)
A silver/palladium relay catalyzed 1,3-dipole annulation/allylation reaction of iminoesters and Baylis-Hillman acetates for the construction of fully substituted allyl imidazolidines is reported. The reaction of both iminoesters and Baylis-Hillman acetate
On the development of a nucleophilic methylthiolation methodology
Carvalho, Bernardo Basbaum Portinho De Puga,Amaral, Adriane Antonia Pereira,De Castro, Pedro P?ssa,Ferreira, Fernanda Cerqueira Moreira,Horta, Bruno Araújo Cautiero,Amarante, Giovanni Wilson
, p. 5420 - 5426 (2020/08/03)
Methylthiolation reactions are usually explored to access organosulfur compounds using methanethiol, an extremely flammable and toxic compound. Herein, methylthiomethyl esters were successfully applied as novel methylthiolation reagents in a low cost, transition-metal-free methodology. These reagents allowed the methylthiolation of a wide scope of chalcones, acyl ester derivatives and Morita-Baylis-Hillman acetates with good group tolerance, affording the methylthiolated products in moderate to excellent yields. The reaction mechanism was investigated through several control experiments, as well as by theoretical calculations employing Density Functional Theory. The results strongly support that a sulfurane and a sulfonium ylide appear as key intermediates and that a Pummerer type rearrangement is also crucial for the formation of this novel reagent. Furthermore, the methylthiolation mechanism is likely to proceed through the nucleophilic attack of the reagent, followed by an entropically favoured step involving the acetate attack to the positively charged species, then releasing the product. This journal is
Regioselective dehydroxytrifluoromethylthiolation of allylic and propargylic alcohols with AgSCF3
Liu, Yin-Li,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 953 - 956 (2019/03/07)
The reaction of easily available Morita–Baylis–Hillman (MBH) alcohols with AgSCF3 in the presence of n-Bu4NI and KI affords primary allylic SCF3 products in high yields and excellent regioselectivities. This regioselective dehydroxytrifluoromethylthiolation protocol could also be extended to propargylic alcohols for the preparation of the primary propargylic SCF3 products.
A Hydrazine Insertion Route to N′-Alkyl Benzohydrazides by an Unexpected Carbon-Carbon Bond Cleavage
Jha, Ajit Kumar,Kumari, Rajkiran,Easwar, Srinivasan
supporting information, p. 8191 - 8195 (2019/10/16)
A serendipitous carbon-carbon bond cleavage in the reaction of benzoyl acrylates, derived from Morita-Baylis-Hillman adducts, with hydrazines delivered new N′,N′-disubstituted benzohydrazides. The reaction features a regioselective formation of two carbon
Design, synthesis, biological evaluation and cocrystal structures with tubulin of chiral β-lactam bridged combretastatin A-4 analogues as potent antitumor agents
Zhou, Pengfei,Liang, Yuru,Zhang, Hao,Jiang, Hao,Feng, Kechang,Xu, Pan,Wang, Jie,Wang, Xiaoming,Ding, Kuiling,Luo, Cheng,Liu, Mingming,Wang, Yang
, p. 817 - 842 (2018/01/10)
A diverse of chiral β-lactam bridged analogues of combretastatin A-4 (CA-4), 3-substituted 1,4-diaryl-2-azetidinones, were asymmetrically synthesized and biologically evaluated, leading to identify a number of potent anti-proliferative compounds represent
Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita-Baylis-Hillman Adducts
Qi, Jifeng,Zheng, Jing,Cui, Sunliang
supporting information, p. 1355 - 1358 (2018/03/09)
An Fe(III)-catalyzed hydroallylation of unactivated alkenes with Morita-Baylis-Hillman adducts via an Fe-catalyzed process is described. A variety of alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diver
Catalytic Enantioselective Vinylogous Allylic Alkylation of Coumarins
Kayal, Satavisha,Mukherjee, Santanu
supporting information, p. 4944 - 4947 (2017/09/23)
An unprecedented, organocatalytic enantioselective vinylogous γ-allylic alkylation of 4-methylcoumarins has been developed. Using allylic carbonates as the allyl source, this reaction is catalyzed by Lewis basic dimeric Cinchona alkaloid (QD)2P
Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS)
Barcelos, Rosimeire C.,Zeoly, Lucas A.,Rodrigues, Manoel T.,Ferreira, Bruno R. V.,Eberlin, Marcos N.,Coelho, Fernando
, p. 1557 - 1570 (2015/02/19)
Abstract We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to goo
