Synthesis of enantiomerically pure N-(2,3-dihydroxypropyl)arylamides via oxidative esterification

• Akula Raghunadh,
• Satish S More,
• T. Krishna Chaitanya,
• Yadla Sateesh Kumar,
• Suresh Babu Meruva,
• L. Vaikunta Rao and
• U. K. Syam Kumar

Beilstein J. Org. Chem. 2013, 9, 2129–2136, doi:10.3762/bjoc.9.250

• : 10.3 g (68%); IR (KBr): 725, 1025, 1270, 1388, 1425, 1704, 1766, 2994, 3424 cm−1; 1H NMR (400 MHz, CDCl3) δ 3.10 (s, 1H, OH), 3.95–3.97 (m, 2H, CH2), 4.39–4.40 (m, 1H, CH), 4.40–4.41 (m, 2H, CH2), 7.46 (t, J = 8 Hz, 2H, ArH), 7.55 (t, J = 7.4 Hz, 1H, ArH), 7.73–7.75 (m, 2H, ArH), 7.86–7.88 (m, 2H, ArH

• , ambient, 5 µL, retention times: 18.75 min, 99.0% ee; [α]D25 −7.4 (c 1.01, methanol). (R)-3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl benzoate (5b): Yellow solid: yield: 10.3 g (68%); IR (KBr): 707, 1123, 1271, 1705, 1767, 2944, 3421 cm−1; 1H NMR (400 MHz, CDCl3) δ 3.09 (d, J = 6 Hz, 1H, OH), 3.94–3.97 (m

• was concentrated, and the crude mixture was directly used for column chromatography with 100% ethyl acetate. After column chromatographic purification, the product was isolated as a colorless liquid in 94% yield. (S)-N-(2,3-dihydroxypropyl)benzamide (6a): Viscous liquid: yield: 2.45 g (94%); IR (KBr

The first example of the Fischer–Hepp type rearrangement in pyrimidines

• Inga Cikotiene,
• Mantas Jonusis and
• Virginija Jakubkiene

Beilstein J. Org. Chem. 2013, 9, 1819–1825, doi:10.3762/bjoc.9.212

• trisubstituted 5-nitrosopyrimidines. The detailed investigation of the mechanism of this transformation is in progress and will be published in due course. Experimental IR spectra were run in KBr discs on a Perkin-Elmer FT spectrophotometer Spectrum BX II. 1H and 13C NMR spectra were recorded with a Varian Unity

• chromatography (eluting with a mixture of hexane:EtOAc) to give products 6 and 8. N-Benzyl-2-methylthio-5-nitroso-6-(piperidin-1-yl)pyrimidin-4-amine (6ea): Blue solid; yield 94%; mp 127 °C; IR (KBr): νmax = 3442 (NH) cm−1; 1H NMR (400 MHz, CDCl3, 25 °C) δ 1.77 (br. s, 6H, (CH2)3), 2.49 (s, 3H, SCH3), 4.16 (br

• ; HRMS (ES): [M + Na]+ calcd for C17H21N5NaOS, 366.1359; found, 366.1359. N-Benzyl-2-methylthio-6-morpholino-5-nitrosopyrimidin-4-amine (6eb): Blue solid; yield 84%; mp 101 °C; IR (KBr): νmax = 3179 (NH) cm−1; 1H NMR (400 MHz, CDCl3, 25 °C) δ 2.50 (s, 3H, SCH3), 3.85 (t, J = 4.8 Hz, 4H, N(CH2)2), 4.29 (t

Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O16

• Manas Jana and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 1757–1762, doi:10.3762/bjoc.9.203

• mixture was neutralized with Dowex 50W-X8 (H+) resin, filtered, and concentrated. The crude product was passed through a Sephadex® LH-20 column by using CH3OH/H2O (2:1) as an eluant to give the pure compound 1 (345 mg, 64%). Glass; [α]D25 −6 (c 1.5, H2O); IR (KBr): 3466, 2945, 1632, 1376, 1165, 1067, 697

Mild and efficient cyanuric chloride catalyzed Pictet–Spengler reaction

• Ashish Sharma,
• Mrityunjay Singh,
• Nitya Nand Rai and
• Devesh Sawant

Beilstein J. Org. Chem. 2013, 9, 1235–1242, doi:10.3762/bjoc.9.140

• , 1H), 7.18–7.13 (m, 7H), 5.10 (s, 1H), 3.39–3.32 (m, 1H), 3.17–3.08 (m, 1H), 2.99–2.84 (m, 2H), 2.39 (s, 3H); 13C NMR (CDCl3, 75.5 MHz) δ 138.91, 138.05, 136.00, 134.81, 129.57, 128.57, 127.50, 121.73, 119.42, 118.29, 110.97, 110.15, 57.85, 42.86, 22.63, 21.29, IR (KBr): 3426, 3309, 2924, 2852, 1595

• , 40.52; IR (KBr): 3020, 2924, 1599 cm–1; MS (ES+) m/z: 338.3 [M + H]+. The two Pictet–Spengler substrates employed in the TCT catalyzed cyclization. The Pictet–Spengler reaction of tryptamine with 4-tolualdehyde. Synthesis of the Pictet–Spengler substrate 4. Reaction conditions: (a) K2CO3, DMF, 80 °C, 3

Isotopically labeled sulfur compounds and synthetic selenium and tellurium analogues to study sulfur metabolism in marine bacteria

• Nelson L. Brock,
• Christian A. Citron,
• Claudia Zell,
• Martine Berger,
• Irene Wagner-Döbler,
• Jörn Petersen,
• Thorsten Brinkhoff,
• Meinhard Simon and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 942–950, doi:10.3762/bjoc.9.108

• ), CaCl2 (0.9 g/L), KCl (0.275 g/L), NaHCO3 (0.08 g/L), KBr (0.04 g/L), SrCl2 (17 mg/L), H3BO3 (11 mg/L), Na-silicate (2 mg/L), NaF (1.2 mg/L), (NH4)NO3 (0.8 mg/L), Na2HPO4 (4 mg/L); pH 7.6) at 28 °C with shaking (160 rpm). When necessary, kanamycin sulfate (60 μg/mL) was added after autoclaving. Feeding

Simple synthesis of pyrrolo[3,2-e]indole-1-carbonitriles

• Adam Trawczyński,
• Robert Bujok,
• Zbigniew Wróbel and
• Krzysztof Wojciechowski

Beilstein J. Org. Chem. 2013, 9, 934–941, doi:10.3762/bjoc.9.107

• million referenced to TMS; coupling constants J in hertz. IR spectra were recorded in KBr on a Perkin Elmer PE Spectrum 2000 spectrometer. Electron impact mass spectra (EI, 70 eV) were obtained on AMD-604 and AutoSpec Premier spectrometer. Electrospray mass spectra (ESI) were obtained on 4000 Q-TRAP and

• , 102.16, 109.93, 118.79, 119.02, 120.50, 126.92, 127.66, 128.29, 128.63, 136.43, 139.48, 141.32, 142.22, 168.98; IR (KBr, cm−1) ν: 2979, 2243, 1728, 1603, 1561, 1510, 1461, 1450, 1409, 1373, 1339, 1272, 1244, 1205, 1188, 1130, 1096, 959, 813, 800, 769, 759, 741; EIMS (70 eV) m/z (% relative intensity

• , 121.08, 127.03, 127.64, 128.25, 128.62, 136.39, 139.40, 141.21, 142.19, 202.77; IR (KBr, cm−1) ν: 2915, 2250, 2240, 1714, 1607, 1559, 1517, 1504, 1451, 1400, 1330, 1257, 1238, 1170, 1081, 1060, 1006, 948, 817, 733; EIMS (70 eV) m/z (% relative intensity): 391 (3) [M]+∙, 357 (11), 92 (8), 91 (100); HRMS

Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction

• Qin Fu and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 918–924, doi:10.3762/bjoc.9.105

• limitation of the reaction was established. The N-alkylation of the isatins is usually accompanied by the formation of spiro epoxyoxindoles. Experimental Reagents and apparatus: Melting points were taken on a hot-plate microscope apparatus. IR spectra were obtained on a Bruker Tensor 27 spectrometer (KBr

• analysis. 3'-benzoylspiro[indoline-3,2'-oxiran]-2-one (3a) [32]: White solid, yield: 83%; mp 158–159 °C; IR (KBr) ν: 3457, 3180, 2972, 1735, 1676, 1620, 1597, 1469, 1335, 1219, 1041, 1013, 927, 850, 794 cm−1; 1H NMR (600 MHz, DMSO-d6) δ cis-isomer: 11.04 (s, 1H, NH), 7.88 (d, J = 7.8 Hz, 2H, ArH), 7.66 (t

• reaction was quenched with water. The solvent was evaporated under reduced pressure. The residue was recrystallized from ethanol to give the pure product for analysis. 3'-benzoyl-1-(2-oxo-2-phenylethyl)spiro[indoline-3,2'-oxiran]-2-one (4a): White solid, yield: 93%; mp 188–189 °C; IR (KBr) ν: 3449, 2929

Synthesis of functionalized spiro[indoline-3,4’-pyridines] and spiro[indoline-3,4’-pyridinones] via one-pot four-component reactions

• Li-Juan Zhang,
• Qun Wu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 846–851, doi:10.3762/bjoc.9.97

• reactions were monitored by TLC. Melting points were taken on a hot-plate microscope apparatus. IR spectra were obtained on a Bruker Tensor 27 spectrometer (KBr disc). NMR spectra were recorded with a Bruker AV-600 spectrometer. HPLC–MS were measured with a Fennigan LCQ Deca XP MAX instrument. High

Direct alkenylation of indolin-2-ones by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles: a novel approach

• Sandeep Kumar,
• Ramendra Pratap,
• Abhinav Kumar,
• Brijesh Kumar,
• Vishnu K. Tandon and
• Vishnu Ji Ram

Beilstein J. Org. Chem. 2013, 9, 809–817, doi:10.3762/bjoc.9.92

• Perkin-Elmer AX-1 spectrophotometer in KBr disc and are reported in wave number (cm−1). ESIMS spectrometers were used for mass spectra analysis. Synthesis of 1-phenyl-3-(methylthio)-5H-dibenzo[d,f][1,3]diazepin-6(7H)-one (5) A mixture of indoline-2-one (4, 1.1 mmol) and 2-pyranone (3, 1.0 mmol) and t

Ring-opening reaction of 2,5-dioctyldithieno[2,3-b:3',2'-d]thiophene in the presence of aryllithium reagents

• Hao Zhong,
• Jianwu Shi,
• Jianxun Kang,
• Shaomin Wang,
• Xinming Liu and
• Hua Wang

Beilstein J. Org. Chem. 2013, 9, 767–774, doi:10.3762/bjoc.9.87

• ), 1.40–1.27 (m, 20H), 0.90–0.87 (m, 6H); 13C NMR (100 MHz, CDCl3) δ 183.03, 155.28, 150.54, 144.49, 139.86, 137.93, 136.87, 128.83, 128.30, 127.74, 127.16, 126.06, 126.02, 31.71, 31.12, 30.85, 30.56, 30.31, 29.14, 29.11, 29.06, 29.04, 28.98, 28.82, 22.54, 14.01; IR (KBr): 2955, 2926, 2855 (C-H), 1661 (C

• , 20.92, 14.07; IR (KBr): 2956, 2926, 2855 (C-H), 1661 (C=O) cm−1; HRMS–EI m/z: [M+ + Na] calcd for C32H44OS3Na, 563.2430; found, 563.2437. Synthesis of 2'-(4-methoxylphenylsulfanyl)-5,5'-dioctyl-[3,3'-bithiophene]-2-carbaldehyde (3c): The same procedure was used as for the synthesis of 3b. From the

• –0.86 (m, 6H); 13C NMR (100 MHz, CDCl3) δ 183.34, 158.98, 155.41, 149.24, 144.91, 137.82, 136.78, 131.34, 129.42, 128.46, 127.50, 127.47, 114.57, 55.21, 31.76, 31.17, 31,02, 30.68, 30,29, 29.19, 29.11, 29.03, 28.94, 22.59, 14.06; IR (KBr): 2958, 2926, 2856 (C-H), 1661 (C=O) cm−1; HRMS–EI m/z: [M+ + Na

4-Pyridylnitrene and 2-pyrazinylcarbene

• Curt Wentrup,
• Ales Reisinger and
• David Kvaskoff

Beilstein J. Org. Chem. 2013, 9, 754–760, doi:10.3762/bjoc.9.85

• ) formation of the ylide 26 and hence the ketenimine 27 becomes the dominant reaction under the conditions of matrix photolysis. Experimental General The apparatus and procedures for preparative FVT [18] and for Ar matrix isolation [11][19][20] were as previously described. KBr and CsI windows were used for

3-Pyridylnitrene, 2- and 4-pyrimidinylcarbenes, 3-quinolylnitrenes, and 4-quinazolinylcarbenes. Interconversion, ring expansion to diazacycloheptatetraenes, ring opening to nitrile ylides, and ring contraction to cyanopyrroles and cyanoindoles

• Curt Wentrup,
• Nguyen Mong Lan,
• Adelheid Lukosch,
• Pawel Bednarek and
• David Kvaskoff

Beilstein J. Org. Chem. 2013, 9, 743–753, doi:10.3762/bjoc.9.84

• ] were as previously described. KBr and CsI windows were used for IR spectroscopy. FVT products were isolated in liquid nitrogen (77 K) in the preparative thermolysis, and at 22–25 K in Ar matrices for IR experiments. IR spectra of the Ar matrices were measured at 7–10 K with a resolution of 1 cm−1

• , J = 8.2 Hz, J = 1.2 Hz, 1H), 7.53–7.47 (m, 3H); 13C NMR (DMSO-d6) 151.4, 144.0, 137.3, 132.2, 129.6, 129.1, 128.9, 128.7, 127.9, 127.5, 127.4, 126.7, 124.9; IR (KBr): 3030 (w), 2100 (s), 1590 (w), 1485 (m), 1415 (s), 1340 (s), 1288 (m), 1270 (s), 1255 (m), 1245 (m), 1230 (m), 955 (m), 895 (s), 860

• -cyanopyrrole (25): Retention time 63 min. 1H NMR (CDCl3) 8.4 (br, 1H), 5.95 (m, 1H), 2.38 (s, 3H), 2.20 (s, 3H); IR (KBr): 3470 (br), 2210 (s), 1600 (w), 1430 (w), 1050 (m), 780 (m); UV (EtOH) λmax: 245 nm; MS m/z: 120 (M+, 67), 119 (100), 106 (28), 105 (71), 78 (10), 65 (3). The spectra data were in agreement

Synthesis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones and novel ring contraction and fusion reaction of 3H-spiro[1,3-thiazole-2,1'-cyclohexanes] into 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones

• Lidia S. Konstantinova,
• Kirill A. Lysov,
• Ljudmila I. Souvorova and
• Oleg A. Rakitin

Beilstein J. Org. Chem. 2013, 9, 577–584, doi:10.3762/bjoc.9.62

• Kofler hot-stage apparatus and are uncorrected. IR spectra were recorded on a Specord M-80 instrument in KBr pellets. 1H NMR were recorded on a Bruker WM 250 spectrometer (250 MHz), and 13C NMR spectra were recorded on a Bruker AM 300 (75.5 MHz) in CDCl3 solution. J-values are given in hertz (Hz). Mass

A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate

• Mohammad Piltan,
• Loghman Moradi,
• Golaleh Abasi and
• Seyed Amir Zarei

Beilstein J. Org. Chem. 2013, 9, 510–515, doi:10.3762/bjoc.9.55

• . Experimental General The reagents and solvents used in this work were obtained from Aldrich and Fluka and were used without further purification. Mp: Electrothermal-9100 apparatus. IR spectra (KBr): Shimadzu IR-460 spectrometer; in reciprocal centimeters (cm−1). 1H and 13C NMR spectra: Bruker DRX-250.1 Avance

• (4a): Grey solid, mp 247–249 °C (dec), 0.57 g, yield 91%; IR (KBr) (vmax/cm−1): 3290 (NH), 1730 (C=O), 1726 (C=O), 1695 (C=O), 1282 (C–O); 1H NMR (250.1 MHz, DMSO-d6) δ 1.21 (t, 3J = 7.1 Hz, 3H, CH3), 3.78 (s, 3H, OCH3), 4.20 (q, 3J = 7.1 Hz, 2H, OCH2), 7.08–7.17 (m, 3H, CH), 8.14 (d, 3J = 8.2 Hz, 1H

• (7), 285 (9), 283 (14), 269 (36); anal. calcd for C16H14N2O5 (314.29): C, 61.14; H, 4.49; N, 8.91; found: C, 61.28; H, 4.37; N, 8.97. Diethyl 4-oxo-4,5-dihydropyrrolo[1,2-a]quinoxaline-1,3-dicarboxylate (4b): Grey solid, mp 245–247 °C (dec), 0.59 g, yield 90%; IR (KBr) (vmax/cm−1): 3287 (NH), 1726 (C

A peptidic hydrogel that may behave as a “Trojan Horse”

• Nicola Castellucci,
• Giorgio Sartor,
• Natalia Calonghi,
• Carola Parolin,
• Giuseppe Falini and
• Claudia Tomasini

Beilstein J. Org. Chem. 2013, 9, 417–424, doi:10.3762/bjoc.9.44

• a Nicolet 210 FT-infrared spectrometer. All spectra were obtained from 3 mM solutions in dry CH2Cl2 at 297 K or from a 1% solid mixture with dry KBr. All compounds were dried in vacuo and all the sample preparations were performed in a nitrogen atmosphere. Routine NMR spectra were recorded with

A new family of four-ring bent-core nematic liquid crystals with highly polar transverse and end groups

• Kalpana Upadhyaya,
• Venkatesh Gude,
• Golam Mohiuddin and
• Rao V. S. Nandiraju

Beilstein J. Org. Chem. 2013, 9, 26–35, doi:10.3762/bjoc.9.4

• distilled and dried before use. Micro analysis of C and H elements were determined on Carlo-Erba 1106 elemental analyzer. IR spectra were recorded on Shimadzu IR Prestige-21, FTIR-8400S (νmax in cm−1) as KBr disks. The 1H nuclear magnetic resonance spectra were recorded on NMR spectrometers (Bruker DPX-400

• as a yellow solid. Yield = 0.30 g (58%); IR (KBr) νmax: 3186, 2951, 2864, 2221, 1741, 1604, 1512, 1490, 1384, 1344, 1288, 1220, 1192, 1163, 1107, 744 cm−1; 1H NMR (400 MHz, CDCl3) δ 13.46 (s, 1H, -OH), 8.55 (s, 1H, -CH=N-), 7.86 (dd, J = 2.0, 7.6 Hz, 1H, ArH), 7.75 (dd, J = 2.4 Hz, 8.8 Hz, 2H, ArH

• obtain the yellow solids. Yield of 1b = 0.32 g, 60%, yield of 1c = 0.30 g, 55% ; yield of 1d = 0.31 g, 56%; yield of 1e = 0.33 g, 61%; yield of 1f = 0.45 g, 65%. 4'-Cyano-[1,1'-biphenyl]-4-yl 3-((4-(pentyloxy)-2-hydroxybenzylidene)amino)-2-chlorobenzoate (1b): IR (KBr) νmax: 3186, 2951, 2864, 2218, 1739

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

• Yan Sun,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2

• spectra were obtained on a Bruker Tensor27 spectrometer (KBr disc). HRMS were measured on an AB 5800 MALDI–TOF/TOF instrument. X-ray data were collected on a Bruker Smart APEX-2 diffractometer. Typical procedure for the synthesis of spiro[dihydropyridine-oxindoles] 1a–1l from the three-component reaction

• , 128.1, 127.3, 127.2, 124.5, 124.4, 117.6, 113.9, 112.5, 108.6, 108.0, 56.0, 55.1, 50.5, 43.1, 32.8, 24.3, 20.5, 18.5; IR (KBr) ν: 3237, 3112, 3060, 2917, 1686, 1603, 1540, 1494, 1378, 1336, 1288, 1229, 1161, 1114, 1037, 859, 818 cm−1; HRMS–ESI (m/z): [M − H]− calcd. for C28H23N2O3: 435.1714; found

• , 179.2, 165.7, 155.3, 141.4, 137.9, 130.3, 127.7, 124.6, 123.9, 121.8, 117.4, 113.3, 112.9, 109.2, 108.1, 55.2, 50.9, 32.8, 24.2; IR (KBr) ν: 3203, 3108, 2966, 2925, 2833, 1703, 1661, 1590, 1538, 1494, 1388, 1330, 1288, 1251, 1194, 1162, 1124, 1039, 911, 857, 805 cm−1; HRMS–ESI (m/z): [M − H]− calcd. for

Convergent synthesis of the tetrasaccharide repeating unit of the cell wall lipopolysaccharide of Escherichia coli O40

• Abhijit Sau and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2012, 8, 2053–2059, doi:10.3762/bjoc.8.230

• ); IR (KBr): 3293, 2845, 2110, 1497, 1454, 1365, 1310, 1119, 1065, 779, 659, 599 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.43–7.23 (m, 15H, Ar-H), 4.98 (d, J = 12.5 Hz, 1H, PhCH2), 4.75 (d, J = 12.5 Hz, 1H, PhCH2), 4.61, 4.58 (2 d, J = 12.0 Hz, 2H, PhCH2), 4.48 (br s, 1H, H-1), 4.45 (d, J = 12.0 Hz, 1H, PhCH2

• pressure to give the crude product. The crude product was purified over SiO2 by using hexane–EtOAc (7:1) as eluant to give pure compound 9 (1.6 g, 74%). White solid; mp 67–68 °C; [α]D25 +39 (c 1.0, CHCl3); IR (KBr): 3417, 3063, 2870, 1774, 1715, 1610, 1495, 1485, 1385, 1216, 1099, 1023, 914, 753, 719 cm−1

• %). White solid; mp 65–66 °C; [α]D25 +34 (c 1.0, CHCl3); IR (KBr): 3423, 3063, 3030, 2871, 2105, 1776, 1744, 1715, 1497, 1454, 1389, 1239, 1102, 1060, 874, 737, 721, 697, 600, 530 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.76–6.96 (m, 49H, Ar-H), 5.52 (d, J = 3.5 Hz, 1H, H-1D), 5.42 (d, J = 8.0 Hz, 1H, H-1C), 5.25

An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives

• Wentao Gao,
• Guihai Lin,
• Yang Li,
• Xiyue Tao,
• Rui Liu and
• Lianjie Sun

Beilstein J. Org. Chem. 2012, 8, 1849–1857, doi:10.3762/bjoc.8.213

• this possibility. Experimental All chemicals (AR graded) were commercially available and used without further purification. The melting points were determined by using a WRS-1B melting-points apparatus and were uncorrected. The IR spectra were obtained as KBr pellets in the range of 400–4000 cm−1 on a

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

• Jing Sun,
• Hong Gao,
• Qun Wu and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2012, 8, 1839–1843, doi:10.3762/bjoc.8.211

• -plate microscope apparatus. IR spectra were obtained on a Bruker Tensor 27 spectrometer (KBr disc). NMR spectra were recorded with a Bruker AV-600 spectrometer with CDCl3 as solvent and TMS as internal standard (600 and 150 MHz for 1H and 13C NMR spectra, respectively). HPLC/MS were measured on a

Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives

• Zhi-Cong Geng,
• Jian Chen,
• Ning Li,
• Xiao-Fei Huang,
• Yong Zhang,
• Ya-Wen Zhang and
• Xing-Wang Wang

Beilstein J. Org. Chem. 2012, 8, 1710–1720, doi:10.3762/bjoc.8.195

• , 28.19; IR (KBr) νmax: 3354.8, 2980.4, 2934.2, 2854.2, 1728.7, 1705.9, 1600.2, 1518.9, 1456.0, 1367.7, 1345.9, 1311.6, 1243.1, 1145.0, 990.9, 853.5, 758.4 cm−1; HRMS–ESI (m/z): [Na]+ calcd for C19H27N3O7, 432.1741; found, 432.1724. Important heterocycles containing pyrazolidine or pyrazoline structures

Polysiloxane ionic liquids as good solvents for β-cyclodextrin-polydimethylsiloxane polyrotaxane structures

• Narcisa Marangoci,
• Rodinel Ardeleanu,
• Laura Ursu,
• Constanta Ibanescu,
• Maricel Danu,
• Mariana Pinteala and
• Bogdan C. Simionescu

Beilstein J. Org. Chem. 2012, 8, 1610–1618, doi:10.3762/bjoc.8.184

• stirred solution of PDMS-Im (26.59 g) in acetonitrile (70 mL). The reaction mixture was stirred for 5 d at 30 °C. The solvent was removed by vacuum distillation [34][35]. FTIR (KBr, cm−1): 3064 and 3032 (Ar-H), 2962 and 2858 (C-H), 1676 (C=N), 1456 and 192 (C=C), 1261 (Si-C), 1091–1000 (Si-O-Si), 802 (Si

• 10 °C/min was applied. Nitrogen purge gas was used as an inert atmosphere at a flow rate of 50 mL/min. The apparatus was temperature- and sensitivity-calibrated with indium, according to standard procedures. FTIR spectra FTIR spectra were recorded on a Bruker Vertex 70 FTIR spectrometer from KBr

Reactions of nitroxides XIII: Synthesis of the Morita–Baylis–Hillman adducts bearing a nitroxyl moiety using 4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl as a starting compound, and DABCO and quinuclidine as catalysts

• Jerzy Zakrzewski

Beilstein J. Org. Chem. 2012, 8, 1515–1522, doi:10.3762/bjoc.8.171

• intensity): M+ 226 (16), 194 (10), 154 (15), 141 (7), 140 (17), 139 (21), 124 (84), 109 (95), 98 (6), 95 (8), 82 (21), 81 (20), 69 (11), 68 (20), 67 (19), 55 (100), 41 (34); HRMS–EI (m/z): calcd for C12H20NO3, 226.14432; found, 226.14401; IR (KBr): 1720 (C=O), 1635 (C=C) cm−1. MBH adducts 5; general

• : 312.21674; mass spectrum (ESI, m/z, %) 335 (100, [M + Na]+) 140 (46); HRMS–ESI (m/z): calcd for C19H26NO4Na, 335.2073; found, 335.2067; IR (KBr): 1701 (C=O), 1633 (C=C) cm−1. 4-(2-((tert-Butyl)hydroxymethyl)acryloyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl (5b): Yield (quinuclidine): 41 mg (33%); red oil

• ; found, 312.21818; ESIMS m/z (% relative intensity): [M + Na]+ 335 (100); HRMS–ESI (m/z): [M + Na]+ calcd for C17H30NO4Na, 335.2073; found, 335.2042; IR (KBr): 1706 (C=O) 1627 (C=C) cm−1. 4-(2-((Trichloromethyl)hydroxymethyl)acryloyloxy)-2,2,6,6-tetramethylpiperidine-1-oxyl (5c): Yield (DABCO): 72 mg (48

Synthesis and characterization of low-molecular-weight π-conjugated polymers covered by persilylated β-cyclodextrin

• Aurica Farcas,
• Ana-Maria Resmerita,
• Andreea Stefanache,
• Mihaela Balan and
• Valeria Harabagiu

Beilstein J. Org. Chem. 2012, 8, 1505–1514, doi:10.3762/bjoc.8.170

• soluble in THF, CH2Cl2, CHCl3 and toluene. FTIR (KBr, cm−1): 3447, 2957, 2923, 1608, 1415, 1364, 1251, 1144, 1096, 1049, 966, 885, 841, 748, 687, 542, 475, 434. 1H NMR (CDCl3): 7.67–7.57 (m, 6 H), 7.33–7.24 (m, 4H), 5.13–4.95 (m, 7H, H1), 4.95–4.79 (m, OH2+3), 3.96–3.53 (m, 42H, H2–6), 2.04 (s, 4H), 1.25

• sample was insoluble in petroleum ether. FTIR (KBr, cm−1): 3428, 3065, 2923, 2851, 1719, 1606, 1465, 1261, 1067, 880, 817, 721, 475, 434. 1H NMR (CDCl3): 7.68–7.58 (m, 6 H), 7.34–7.24 (m, 4H), 2.05 (m, 4H), 1.26–1.10 (m, 24H), 0.91–0.80 (d, 6H). 1H NMR spectrum (CDCl3) of the BTc inclusion complex. FTIR

• spectra (KBr pellet) of PDOF-BT (A) and PDOF-BTc (B) copolymers. 1H NMR spectrum of PDOF-BT copolymer (CDCl3). 1H NMR spectrum of PDOF-BTc copolymer (CDCl3). DSC curves of BTc and PDOF-BTc from second-heating DSC measurements. Thermogravimetric curves (TG) for BTc, PDOF-BT, and PDOF-BTc compounds. High

A novel asymmetric synthesis of cinacalcet hydrochloride

• Veera R. Arava,
• Laxminarasimhulu Gorentla and
• Pramod K. Dubey

Beilstein J. Org. Chem. 2012, 8, 1366–1373, doi:10.3762/bjoc.8.158

• were recorded on a Perkin-Elmer spectrophotometer as KBr pellets or neat. Analytical TLC is conducted on E-Merck 60 F254 aluminium-packed silica gel plates (0.2 mm). Developed plates were visualized under UV light or in an iodine chamber. Chiral HPLC analyses were recorded with on a Waters Alliance

• yellow crystalline solid. The remaining product from the mother liquor was isolated from column chromatography with n-hexane/ethyl acetate (9:1). Yield = 22.0 g (68%); mp 97.0–98.2 °C; [α]D23 −116.8 (c 1.0, CHCl3); chiral purity (HPLC): 99.97% (R-isomer) and 0.03% (S-isomer); IR (KBr): 3220 (sharp

• %); purity (HPLC): 99.9%; IR (KBr): 3220 (–COOH), 1682 (–CO–) cm−1; 1H NMR (CDCl3/TMS) δ 6.50 (d, 1H, –CH), 7.54 (t, 1H, ArH), 7.63 (d, 2H, –CH and ArH), 7.68–7.75 (m, 2H, ArH); 13C NMR (CDCl3/TMS) δ 172.62, 147.10, 140.03, 135.72, 134.15, 131.0, 129.80, 129.07, 129.03, 127.09, 125.71. Preparation of 3-(3