-4 6- 许招会, 熊 Vol. 37 No Journal of Jiangxi Normal University Natural Science Jul Scheme 1.
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1 37 4 Vol 37 No Journal of Jiangxi Normal UniversityNatural Science Jul 许招会, 熊 斌, 雷志伟 LaPW 12 O % 20 ~ 40 min 87 6% ~ 94 3% LaPW 12 O 40 LaPW 12 O O A 0 5% LaPW 12 O Scheme 1 Grignard reagent Diels-Alder 5- Scheme K 3 PO 7 4 ZnCl 8 2 / 1 1 Michael BuchiB-540 P W Bruker 400 MHZ CDCl 3 TMS H NMR 400 MHz C NMR 125 MHz FT-IR-8400 KBr SPD-6AV kj YC10A
2 cm H NMR δ8 32 s 1H SPD-6AV 8 19 d J = 8 97 Hz 2H 6 98 d J = 8 97 Hz C 8 50 m 3 2 mm 40 2H3 90 s 3H 2 23 ~ 2 18 m 4H 1 90 ~ 254 nm 1 85 m 4H 13 C NMR δ V V= = 1 ml /min !L Sepu PWA cm H NMR δ8 41 s 1H ~ d J = 8 82 Hz 2H 8 06 d J = 8 70 Hz 2H ~ 2 23 m 4H 1 95 ~ 1 90 m 4H 120 min 13 C NMRδ LaPW 12 O 40 nh 2 O h LaPW 12 O e IR KBr 3a ~ 3h υ 50 ml 5 mmol max cm H NMR 5 mmol δ8 75 s 1H d J = 8 22 Hz 1H 7 78 ~ 7 62 m 2H 7 49 LaPW 12 O 40 5% 20 ~ d J = 7 56 Hz 1H2 24 ~ 2 21 m 4H1 91 ~ 40 min 10 ml 1 89 m 4H 3a ~ 13 C NMR δ h a IR KBr υ max cm H NMR 300 MHz CDCl 3 δ8 37 s 1H 8 02 d J = 7 14 Hz 2H7 56 ~ 7 47 m 3H2 22 s 4H 1 89 s 4H 13 C NMR δ b IR KBr υ max cm H NMR δ8 35 s 1H 8 12 d J = 8 82 Hz 2H 6 94 d J = 8 82 Hz 2H 2 24 ~ 2 19 m 4H1 90 ~ 1 85 m 4H 13 C NMR δ c IR KBr υ max d IR KBr υ max f IR KBr υ max cm H NMR δ8 33 s 1H8 14 dd J = Hz 2H7 16 t J = 8 61 Hz 1H 2 24 ~ 2 19 m 4H 1 91 ~ 1 86 m 4H 13 C NMR δ Lewis FeCl 3 1 Entries 1 H 3 PW 12 O 40 LaPW 12 O 40 2 LaPW 12 O 40
3 % 1 Entries 2 ~ 90 3% 3 8% 0 1% 1 Entries 4 ~ % 1 Entries 1 Entries 9 ~ % 30 min 1 a Entry Solvent Catalyst Molar fraction of catalyst /% Temperature / Time /min b Yield /% 1 C 2 H 5 OH FeCl 3 5 Reflux C 2 H 5 OH H 3 PW 12 O 40 5 Reflux C 2 H 5 OH LaPW 12 O 40 5 Reflux CH 3 CN LaPW 12 O 40 5 Reflux THF LaPW 12 O 40 5 Reflux CH 2 Cl 2 LaPW 12 O 40 5 Reflux C 6 H 6 LaPW 12 O 40 5 Reflux H 2 O LaPW 12 O 40 5 Reflux None LaPW 12 O None LaPW 12 O None LaPW 12 O None LaPW 12 O None None None LaPW 12 O None LaPW 12 O None LaPW 12 O None LaPW 12 O a Reaction conditionsbenzaldhyde5 mmol2 2-butylidene-1 3-dioxane-4 6-dione5 mmoland catalyst and solvent10 ml or solvent-free conditionsb isolated yield 2 2 LaPW 12 O 87 6% ~ 94 3% Michael LaPW 12 O 40 2 LaP 12 WO a Product Ar Yield /% Time /min m p c / Mass fraction /% 3a C 6 H ~ 8888 ~ b 4-HO C 6 H ~ ~ c 4-CH 3 O C 6 H ~ 8583 ~ d 4-NO 2 C 6 H ~ ~ e 2-NO 2 C 6 H ~ ~ f 4-F C 6 H ~ g 4-Cl C 6 H ~ ~ h 4-CH 3 2 N C 6 H ~ ~ Reaction conditionsbenzaldhyde5 mmol2 2-butylidene-1 3-dioxane-4 6-dione5 mmol LaP 12 WO 40 5% solvent-free b isolated yieldc melting points are uncorrected
4 % 91 4% % 88 3% Knoevenagel LaPW 12 O 40 Knoevenagel β H 2 O Scheme Scheme 2 Knoevenagel LaPW 12 O 40 7Desai U V Pore D M Mane R B et al One pot synthesis of monoalkylated and mixed dialkylated Meldrum s acid Jacobs R T Wright A D Smith F X Condensation of monosubstituted isopropylidene malonates with mannich bases J J Org Chem Bruns RWernicke A Koll P Application of the reaction of D-glucose with Meldrum s acidtotal synthesis of the styryl lactones + -goniofufurone and + -7-epi-goniofufurone J Tetrahedron J Watanabe T Knpfel T F Carreira E M Asymmetric conjugate addition reactions of Meldrum s acid derived acceptors employing chiral phosphoramidite ligands J Org Lett Fillion E Dumas A M Hogg S A Modular synthesis of tet- LaPW 12 O 40 rahydrofluorenones from 5-alkylidene Meldrum s acids J J Org Chem Huang Xian Xie Lin One pot synthesis of 5-monosubstituted Meldrum s acid J Synth Commun derivatives J SynthCommun Rao Pengshan Venkataratnam R V Zinc chloride as a new catalyst for knoevenagel condensation J Tetrahedron Lett Davidson D Bernhard S A The Structure of Meldrum s supposed β-lactonic acid J J Am Chem Soc Corey E J The mechanism of the decarboxylation of α β- and βγ-unsaturated malonic acid derivatives and the course of decarboxylative condensation reactions in pyridine J J Am Chem Soc Kraus G A Krolski M E Synthesis of a precursor to quassimarin J J Org Chem Scuster P Polansky O E Wessely F Zur Kenntnis cyclis-
5 cher Acylale 6 Mitt J Monatsch Chem J 16 J LaOTf J Dumas A M Seed A Zorzitto A K et al A general and practical preparation of alkylidene Meldrum s acids J Tetrahedron Letters J J Solvent-Free Synthesis of 5-Alkenyl-2 2-Butylidene-1 3-Dioxane-4 6-Diones with LaPW 12 O 40 as Catalyst XU Zhao-hui XIONG Bin LEI Zhi-wei College of Chemistry and Chemical Engineering Jiangxi Normal University Nanchang Jiangxi China AbstractEight kinds of 5-alkenyl-2 2-butylidene-1 3-dioxane-4 6-diones were synthesized by the Knoevenagel condensation reaction of aromatic aldehydes with 2 2-pentamethylene -1 3-dioxane-4 6-dione using LaPW 12 O 40 as catalyst without solvent The results indicate that the yields ranged from 87 6% ~ 94 3% when using 5% molar fractionlapw 12 O 40 and reacting at room temperature for 20 ~ 40 min Furthermore a proposed reaction mechanism for the reaction catalyzed by LaPW 12 O 40 was speculated Compared to the classical Knoevenagel condensation reaction the main advantages of the present procedure were milder conditions shorter reaction time and higher yields which afforded an effective method to synthesize 5-alkenyl-isopropylidene malonate derivatines Further study showed that LaPW 12 O 40 was environmentally friendly and reused for four times without any noticeable decrease in the catalytic activity Key words2 2-butylidene-1 3-dioxane-4 6-dioneLaPW 12 O 40 aromatic aldehydescondensation reaction
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