29113-65-3Relevant academic research and scientific papers
nBu4NI-catalyzed C–C bond formation to construct 2-carbonyl-1,4-diketones under mild conditions
Lv, Yunhe,Pu, Weiya,Niu, Jiejie,Wang, Qingqing,Chen, Qian
, p. 1497 - 1500 (2018)
An nBu4NI-catalyzed oxidative cross-dehydrogenative-coupling of β-dicarbonyl compounds with acetone under mild reaction conditions is described. This methodology provides a straightforward pathway to synthesize 2-carbonyl-1,4-diketones and feat
Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights
Pace, Domenic P.,Robidas, Rapha?l,Tran, Uyen P. N.,Legault, Claude Y.,Nguyen, Thanh Vinh
supporting information, p. 8154 - 8171 (2021/06/28)
Substituted pyrans and furans are core structures found in a wide variety of natural products and biologically active compounds. Herein, we report a practical and mild catalytic method for the synthesis of substituted pyrans and furans using molecular iodine, a simple and inexpensive catalyst. The method described is performed under solvent-free conditions at an ambient temperature and atmosphere, thus offering a facile and practical alternative to currently available reaction protocols. A combination of experimental studies and density functional theory calculations revealed interesting mechanistic insights into this seemingly simple reaction.
Synthesis, insecticidal activities, and SAR studies of novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives
Li, Huan,Liu, Hang,Zhang, Yan,Yang, Na,Xiong, Lixia,Li, Zhengming,Wang, Baolei
, p. 2893 - 2898 (2021/05/19)
Diamide compounds such as chlorantraniliprole, a famous anthranilic diamide insecticide targeting the insect ryanodine receptor (RyR), have received continuous attention in pesticide research during the past 15 years owing to their excellent insecticidal potentials. With the aim of discovering new heterocyclic pesticides used for crop protection, based on the structural information of compound M from the reported pharmacophore-based virtual screening for RyR insecticides and diamide compound, a series of new heterocyclic mono-, di-, and tri-amide derivatives containing piperazine moiety have been synthesized in this paper. The new compounds were identified and confirmed by melting point, 1H NMR, 13C NMR and HRMS. Compound M was firstly validated for insecticidal activities, and the new synthesized compounds were all made comprehensive insecticidal evaluations against diamondback moth and oriental armyworm. The bioassay results showed that some of the compounds exhibit favorable insecticidal potentials, particularly some novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives such as 8g, 14a, 15a, 15g, 15i, 15j, 15k, 15l, and 15m could be used as new insecticidal leading structures for further study (e.g., towards diamondback moth, 15i-15m LC50: 0.0022?0.0081 mg/L). The structure-activity relationships of the compounds discussed in detail provide useful guidance for further design and development of new insecticides.
Synthesis of 3-Carbonyl Trisubstituted Furans via Pd-Catalyzed Aerobic Cycloisomerization Reaction: Development and Mechanistic Studies
Barboza, Amanda A.,Neto, Attilio Chiavegatti,Rosset, Isac G.,Jardim, Guilherme A. M.,Ferreira, Marco A. B.
, p. 3923 - 3942 (2021/04/02)
Herein, we report the synthesis of 3-carbonyl-trisubstituted furans via Pd-catalyzed oxidative cycloisomerization reactions of 2-alkenyl-1,3-dicarbonyl scaffolds, using molecular oxygen as the sole oxidant to regenerate active palladium catalytic species, featuring good functional tolerance and mild reaction conditions. Deep investigation of intermediates and transition states of the reaction mechanism were conducted via experimental and DFT studies, providing a detailed mechanistical profile. The new developed methodology presents a greener alternative to Wacker-type cycloisomerizations and avoids the use of stoichiometric amounts of oxidants and strong acid additives.
Acid-Promoted One-Pot Synthesis of Substituted Furan and 6-Methylpyrazin-2(1 H)-one Derivatives via Allene Intermediate Formed in Situ
Lei, Jie,Xu, Zhi-Gang,Tang, Dian-Yong,Li, Yong,Xu, Jia,Li, Hong-Yu,Zhu, Jin,Chen, Zhong-Zhu
, p. 292 - 297 (2018/05/24)
Under the acidic conditions, substituted furans were constructed from γ-alkynyl ketones through corresponding allene intermediates in one-pot. The methodology was also tailored to a series of the Ugi reaction products for the synthesis of 6-methylpyrazin-2(1H)-one derivatives. The current method offered significant advantages for the combinatorial applications of these chemical scaffolds.
Iron(III) chloride-catalyzed synthesis of 3-carboxy-2,5-disubstituted furans from γ-alkynyl aryl- and alkylketones
Golonka, Alexander N.,Schindler, Corinna S.
, p. 4109 - 4114 (2017/06/29)
A mild, catalytic method for the synthesis of 3-carboxy-2,5-disubstituted furans is reported proceeding via a 5-exo-dig cycloisomerization reaction. The iron(III) chloride-catalyzed transformation of aryl- and alkyl β-ketoesters enables synthetic access t
Thulium Triflate Catalyzed Hydration of 2-Substituted 4-Alkynones
Chang,Cheng
supporting information, p. 1931 - 1935 (2016/08/09)
We report on a facile synthetic route for the preparation of substituted 1,4-diketones by thulium triflate mediated hydration of substituted 4-alkynones in MeNO2 at 25 °C for five hours. The products were obtained in moderate to high yields.
Bi(OTf)3-mediated cycloisomerization of γ-alkynyl arylketones: Application to the synthesis of substituted furans
Chang, Meng-Yang,Cheng, Yu-Chieh,Lu, Yi-Ju
supporting information, p. 1264 - 1267 (2015/03/14)
A novel Bi(OTf)3-mediated cycloisomerization of γ-alkynyl arylketones 4, 7, or 10 with molecular sieve (MS) in MeNO2 affords 3-substituted furans 3, 8, or 11 at rt for 3 h in moderate to good yields. The method provides mild, less-to
Indium-catalyzed synthesis of furans and pyrroles via cyclization of α-propargyl-β-keto esters
Tsuji, Hayato,Yamagata, Ken-Ichi,Ueda, Yasuyuki,Nakamura, Eiichi
supporting information; experimental part, p. 1015 - 1017 (2011/06/17)
In(OTf)3 or In(NTf2)3 effectively catalyze the cyclo-isomerization reaction of -propargyl - keto esters and their imine analogues to afford trisubstituted furans and pyrroles, respectively. Both terminal and internal alkyn
Furan synthesis through AuCl3-catalysed cycloisomerisation of β-alkynyl β-ketoesters
Rodríguez, Arantxa,Moran, Wesley J.
supporting information; experimental part, p. 2605 - 2607 (2011/06/21)
AuCl3 efficiently catalyses the cycloisomerisation of readily available β-alkynyl β-ketoesters to generate trisubstituted furans. The substrate scope is wide and the reaction is high yielding and operationally simple.
