105479-98-9Relevant academic research and scientific papers
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
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
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
2-Azetidinones: Synthesis and biological evaluation as potential anti-breast cancer agents
Geesala, Ramasatyaveni,Gangasani, Jagadeesh Kumar,Budde, Mahender,Balasubramanian, Sridhar,Vaidya, Jayathirtha Rao,Das, Amitava
, p. 544 - 558 (2016/09/09)
A series of twenty-five 2-azitidinone (β-lactam) derivatives were synthesized and evaluated for anti-cancer properties against breast cancer, MCF-7 and MDA-MB-231. These β-lactam derivatives depicted significant cytotoxicity in cancer cell lines but not i
One-pot synthesis of allyl thioacetate from benzaldehydes and activated alkenes using the Morita-Baylis-Hillman reaction as a key step
Yang, Hae-Won,Choi, Ji-Su,Lee, Sang-Jin,Yoo, Byung-Woo,Yoon, Cheol Min
, p. 134 - 140 (2016/03/30)
An efficient, regioselective and steresoselecitive one-pot protocol for the synthesis of (Z)-S-2-alkoxycarbonyl-3-acylallyl ethanethioates and (E)-S-2-cyano-3-acylallyl ethanethioates from benzaldehydes and activated alkenes (methyl acrylate and acrylonit
Probing the mechanism of allylic substitution of morita-baylis- Hillman acetates (MBHAS) by using the silyl phosphonite paradigm: Scope and applications of a versatile transformation
Kalyva, Maria,Zografos, Alexandros L.,Kapourani, Era,Giambazolias, Evaggelos,Devel, Laurent,Papakyriakou, Athanasios,Dive, Vincent,Lazarou, Yannis G.,Georgiadis, Dimitris
supporting information, p. 3278 - 3289 (2015/03/05)
A P-C bond-forming reaction between silyl phosphonites and Morita-Baylis-Hillman acetates (MBHAs) is explored as a general alternative towards medicinally relevant ?2;-carboxyphosphinic structural motifs. Conversion rates of diversely substituted MBHAs to phosphinic acids 9 or 14that were recorded by using 31P NMR spectroscopy revealed unexpected reactivity differences between ester and nitrile derivatives. These kinetic profiles and DFT calculations support a mechanistic scenario in which observed differences can be explained from the "lateness" of transition states. In addition, we provide experimental evidence suggesting that enolates due to initial P-Michael addition are not formed. Based on the proposed mechanistic scenario in conjunction with DFT calculations, an interpretation of the E/Z stereoselectivity differences between ester and nitriles is proposed. Synthetic opportunities stemming from this transformation are presented, which deal with the preparation of several synthetically capricious phosphinic building blocks, whose access through the classical P-Michael synthetic route is not straightforward.
PYRIDOPYRIMIDINE BASED DERIVATIVES AS POTENTIAL PHOSPHODIESTERASE 3 (PDE3) INHIBITORS AND A PROCESS FOR THE PREPARATION THEREOF
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Paragraph 0082; 0103; 0104; 0106, (2014/08/19)
The present invention provides compounds of formula 1 as potential phosphodiesterase3 (PDE3) inhibitory agents and a process for the preparation thereof. The derivatives of formula 1 can be employed as therapeutics in human and veterinary medicine, where
INDOLIZINONE BASED DERIVATIVES AS POTENTIAL PHOSPHODIESTERASE 3 (PDE3) INHIBITORS AND A PROCESS FOR THE PREPARATION THEREOF
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Paragraph 0077, (2014/10/16)
The present invention provides compounds of general formula A useful as potential phosphodiesterase3 (PDE3) inhibitory agents and a process for the preparation thereof. The derivatives of formula A can be employed as therapeutics in human and veterinary medicine, where they can be used, for example, for the treatment and prophylaxis of the following diseases: heart failure, dilated cardiomyopathy, platelet inhibitors, cancer and obstructive pulmonary diseases.
DMAP-catalyzed [3 + 2] and [4 + 2] cycloaddition reactions between [60]fullerene and unmodified Morita-Baylis-Hillman adducts in the presence of Ac2O
Yang, Hai-Tao,Ren, Wen-Long,Miao, Chun-Bao,Dong, Chun-Ping,Yang, Yang,Xi, Hai-Tao,Meng, Qi,Jiang, Yan,Sun, Xiao-Qiang
, p. 1163 - 1170 (2013/04/10)
One-step DMAP-catalyzed [3 + 2] and [4 + 2] cycloaddition reactions between C60 and unmodified Morita-Baylis-Hillman adducts in the presence of Ac2O have been developed for the easy preparation of cyclopentene- and cyclohexene-fused
