Comptes Rendus Chimie

Sadegh Rostamnia

EtOAc-dispersed magnetic nanoparticles (DMNPs) of γ-Fe2O3 in the single-pot domino preparation of 5-oxo-2-thioxo-3-thiophenecarboxylate derivatives

Le Comité de rédaction

Erratum à l’article « Synthèse prébiotique dans les conditions hydrothermales » par Marie-Paule Bassez [C. R. Chimie 12 (6–7) (2009) 801–807]

Meriem Lamouchi

Erwann Jeanneau

Jérémy Coulm

Arnaud Brioude

Cédric Desroches

Synthesis and properties of mono-O-[(N-(aminoalkyl)aminocarbonyl)-methoxy]thiacalix[4]arenes and novel mono-O-bridged bisthiacalix[4]arene

Mithu Saha

Babulal Das

Amarta Kumar Pal



Greener Synthesis of Pyran derivatives under Ultrasound irradiation using Ni nanoparticles as reusable catalyst in aqueous medium
Mithu Sahaa, Babulal Dasb , Amarta K. Pal*a  
aDepartment of Chemistry, North Eastern Hill University, Mawlai  Campus, Shillong 793022, India.
bDepartment of Chemistry, IIT Guwahati, India

CONTENT
1.	Experimental---------------------------------------------------------2
2.	General Procedure--------------------------------------------------3
3.	Spectral data--------------------------------------------------------4-9
4.	Scanned spectra of 1H and 13C NMR----------------------------10-41





General
Experimental 
Melting points were determined in open capillaries and are uncorrected. IR spectra were recorded on Spectrum BX FT-IR, Perkin Elmer (υmax in cm-1) on KBr disks. 1H NMR and 13C NMR (400 MHz and 100 MHz respectively) spectra were recorded on Bruker Avance II-400 spectrometer in CDCl3 (chemical shifts in δ with TMS as internal standard). Mass spectra were recorded on Waters ZQ-2695. Transmission Electron Microscope (TEM) was recorded on JEOL JSM 100CX. Scanning electron microscope (SEM) was recorded on JSM-6360 (JEOL). XRD was recorded on Bruker D8 XRD instrument SWAX .CHN were recorded on CHN-OS analyzer (Perkin Elmer 2400, Series II). Silica gel G (E-mark, India) was used for TLC. Hexane refers to the fraction boiling between 60 οC and 80 οC. Ultrasonication reaction was carried out in JAC 1500 (Made in Korea)


X-ray crystallography: 
The X-ray diffraction data were collected at 296 K with Mo Kα radiation (λ = 0.71073 Å) using a Bruker Nonius SMART APEX II CCD diffractometer equipped with a graphite monochromator. Smart software was used for data collection and also for indexing the reflections and determining the unit cell parameters; the collected data were integrated using saint software. The structures were solved by direct methods and refined by full-matrix least-squares calculations using SHELXTL software. All the non-H atoms were refined in the anisotropic approximation. (CCDC 836545).


General procedure for the synthesis of pyran derivatives 
A mixture of carbonyl compounds 1 (1 mmol), malononitrile 2 (1 mmol) and activated C-H compounds 3-5 (1 mmol) was taken in a round bottle flask to that nickel nanoparticles (10 mol %), water (2 mL) or water-ethanol mixture (1:1) (2 mL) [in case of 4-hydroxy coumarin 5] was added and irradiated in ultrasound for the time in mentioned in table 2. After completion (TLC), the reaction mixture was cooled, filtered and the solvent was removed under reduced pressure. The residue was extracted with ethyl acetate (3 × 10 mL) and the combined organic extract was washed with water (3 × 10 mL), brine (10 mL) and dried over anhydrous Na2SO4. After removing the solvent the crude product was purified by column chromatography over silica gel (60-120 mesh) using hexane-ethyl acetate as eluent to afford the pure products.









SUPPORTING INFORMATION
1.	Compound 6a
IR (KBr): 3476, 3330, 2196, 1659 cm-1. 1H NMR (DMSO-d6, 400 MHz): δ = 1.76 (s, 3H), 3.27 (brs, 2H), 4.67 (s, 1H), 7.21-7.50 (m, 8H), 7.76 (d, J = 8.0 Hz, 2H). ESI-MS m/z 329 [M + H]+. Anal calcd for: C20H16N4O: C, 73.15; H, 4.91; N, 17.06. Found: C, 73.02; H, 4.82; N, 16.91.
2.	Compound 6b
IR (KBr): 3475, 3326, 2196, 1656 cm-1. 1H NMR (CDCl3+ DMSO-d6, 400 MHz): δ = 1.78 (s, 3H), 2.25 (s, 3H), 4.50 (s, 1H), 6.22 (s, 2H), 7.35 (t, J = 7.8 Hz, 5H), 7.65 (d, J = 8.4 Hz, 4H). 13 C NMR (CDCl3+ DMSO-d6, 100 MHz): δ = 12.4, 20.6, 36.6, 60.1, 98.1, 119.7, 120.2, 125.8, 127.3, 128.7, 128.8, 136.2, 137.3, 139.5, 143.6, 145.6, 158.9. ESI-MS m/z 343 [M + H]+. Anal calcd for C21H18N4O: C, 73.67; H, 5.30; N, 16.36. Found: C, 73.75; H, 5.36; N, 16.48.
3.	Compound 6c
IR (KBr): 3420, 3310, 2196, 1666 cm-1. 1H NMR (CDCl3+ DMSO-d6, 400 MHz): δ = 1.81 (S, 3H), 4.60 (s, 1H), 4.64 (brs, 2H), 6.95-7.42 (m, 7H), 7.56 (d, J = 8.0 Hz, 2H) . ESI-MS m/z 347 [M + H]+. Anal calcd for C20H15 FN4O: C, 69.37; H, 4.37; N, 16.18 Found: C, 69.29; H, 4.48; N, 16.04.
4.	Compound 6d
IR (KBr): 3400, 3320, 2230, 1658 cm-1. 1H NMR (CDCl3+ DMSO-d6, 400 MHz): δ = 1.78 (S, 3H), 4.74 (s, 1H), 6.89 (brs, 2H), 7.21 (t, J = 7.4 Hz, 1H), 7.38-7.45 (m, 4H), 7.70 (d, J = 8.0 Hz, 2H), 8.13 (d, J = 8.8 Hz, 2H). 13 C NMR (CDCl3+ DMSO-d6, 100 MHz): δ = 12.5, 36.8, 57.4, 96.9, 119.4, 120.1, 123.5, 125.9, 128.6, 128.8, 137.2, 143.9, 145.1, 146.5, 150.3, 159.5. ESI-MS m/z 374 [M + H]+. Anal calcd for C20H15N5O3: C, 64.08; H, 4.05; N, 18.76. Found: C, 64.23; H, 4.19; N, 18.67.

5.	Compound 6e
IR (KBr): 3456, 3330, 2196, 1666 cm-1. 1H NMR (CDCl3+ DMSO-d6, 400 MHz): δ = 1.81 (s, 3H), 4.55 (s, 2H), 5.96 (brs, 2H), 7.07 (d, J = 8.4 Hz, 2H), 7.21 (t, J = 7.2 Hz, 1H), 7.37-7.41 (m, 4H), 7.63 (d, J = 8.0 Hz, 2H). ESI-MS m/z 407, 409 [M + H]+. Anal calcd for C20H15 BrN4O: C, 58.98; H, 3.71; N, 13.76. Found: C, 59.06; H, 3.74; N, 13.78.
6.	Compound 6f
IR (KBr): 3456, 3370, 2230, 1660 cm-1. 1H NMR (CDCl3, 400 MHz): δ = 1.82 (s, 3H), 4.58 (s, 1H), 4.66 (brs, 2H), 7.12 (d, J = 8.4 Hz, 2H), 7.25 (d, J = 8.4 Hz, 2H), 7.38 (t, J = 7.4 Hz, 3H), 7.56 (d, J = 8.0 Hz, 2H). ESI-MS m/z 363, 365 [M + H]+. Anal calcd for C20H15ClN4O: C, 66.21; H, 4.17; N, 15.44. Found: C, 65.92; H, 4.24; N, 15.57.
7.	 Compound 6g
IR (KBr): 3429, 3400, 2369, 1653 cm-1. 1H NMR (CDCl3+ DMSO-d6, 400 MHz): δ = 1.81 (s, 3H), 4.67 (s, 1H), 4.74 (brs, 2H), 7.25-7.61 (m, 9H). ESI-MS m/z 354 [M + H]+. Anal calcd for C21H15N5O: C, 71.38; H, 4.28; N, 19.82. Found: C, 71.16; H, 4.44; N, 19.85.
8.	Compound 6h
IR (KBr): 3456, 3363, 2190, 1659 cm-1. 1H NMR (CDCl3+ DMSO-d6, 400 MHz): δ = 1.80 (s, 3H), 4.73 (s, 2H), 6.08 (brs, 2H),7.23-7.67 (m, 7H), 8.03-8.09 (m, 2H). ESI-MS m/z 374[M + H]+. Anal calcd for C20H15N5O3: C, 64.34; H, 4.05; N, 18.76. Found: C, 64.16; H, 3.93; N, 19.03.
9.	Compound 6i
IR (KBr): cm-1. 1H NMR (CDCl3,,400 MHz): δ = 1.81 (s, 3H), 4.67(brs, 2H), 5.23 (s, 1H), 7.12-7.41 (m, 7H), 7.56 (d, J = 8.0 Hz, 2H). ESI-MS m/z 363, 365 [M + H]+. Anal calcd for C20H15 ClN4O: C, 66.21; H, 4.17; N, 15.44. Found: C, 65.96; H, 4.06; N, 15.29.
10.	Compound 7a
IR (KBr): 3428, 3371, 2196, 1659, 1613 cm-1. 1H NMR (CDCl3, 400 MHz): δ = 7.23-7.10 (m, 5H), 4.47 (s, 2H), 4.33 (s, 1H), 2.38 (s, 2H), 2.10-2.20 (m, 2H), 1.04 (s, 3H), 0.97 (s, 3H). 13C NMR (CDCl3, 100 MHz): δ = 195.8, 161.5, 157.4, 143.1, 128.5, 127.5, 127.1, 118.6, 114.0, 63.5, 50.6, 40.6, 35.5, 32.2, 28.8, 27.6. ESI-MS m/z 295 [M + H]+. Anal calcd for C18H18N2O2: C, 73.45; H, 6.16; N, 9.52. Found: C, 73.34; H, 6.13; N, 9.64.
11.	Compound 7b
IR (KBr): 3429, 3330, 2395, 2190, 1679, 1600 cm-1. 1H NMR (CDCl3, 400 MHz): δ = 7.05-7.00 (m, 4H), 4.45 (s, 2H), 4.29 (s, 1H), 2.37 (s, 2H), 2.21 (s, 3H), 2.15 (d, J = 5.6 Hz, 2H), 1.03 (s, 3H), 0.97 (s, 3H).13C NMR (CDCl3, 100 MHz): δ = 196.0, 161.4, 157.3, 140.2, 136.7, 129.3, 127.3, 118.7, 114.1, 63.7, 50.6, 40.6, 35.1, 32.2, 28.9, 27.7, 21.0. ESI-MS m/z 309 [M + H]+. Anal calcd for C19H20N2O2: C, 74.00; H, 6.54; N, 9.08. Found: C, 73.70; H, 6.31; N, 9.02. 
12.	Compound 7c
IR (KBr): 3420, 3323, 2335, 2196, 1659, 1606 cm-1. 1H NMR (CDCl3, 400 MHz): δ = 7.09 (d, J = 8.0 Hz, 2H), 6.75 (d, J = 8.4 Hz, 2H), 4.49 (s, 2H), 4.28 (s, 1H), 3.69 (s, 3H), 2.38 (s, 2H), 2.19-2.09 (m, 2H) 1.03 (s, 3H), 0.96 (s, 3H). ESI-MS m/z 325 [M + H]+. Anal calcd for C19H20N2O3: C, 70.35; H, 6.21; N, 8.64. Found: C, 70.53; H, 6.09; N, 8.80
13.	Compound 7d
IR (KBr): 3421, 3363, 2316, 2196, 1653, 1600 cm-1. 1H NMR (CDCl3, 400 MHz): δ = 7.15-7.12 (m, 2H), 6.92-6.88 (m, 2H), 4.49 (s, 2H), 4.33 (s, 1H), 2.38 (s, 2H), 2.20-2.10 (m, 2H), 1.04 (s, 3H), 0.96 (s, 3H). ESI-MS m/z 313 [M + H]+. Anal calcd for C18H17FN2O2: C, 69.22; H, 5.49; N, 8.97. Found: C, 69.42; H, 5.42; N, 8.88. 

14.	Compound 7e
IR (KBr): 3396, 3323, 2448, 2196, 1666, 1600 cm-1. 1H NMR (CDCl3 + DMSO-d6, 400 MHz): δ = 8.07 (d, J = 8.4 Hz, 2H), 7.37 (d, J = 8.4 Hz, 2H), 6.31 (s, 2H), 4.38 (s, 1H), 2.44 (s, 2H), 2.21-2.07 (m, 2H), 1.05 (s, 3H), 0.95 (s, 3H). ESI-MS m/z 340 [M + H]+. Anal calcd for C18H17N3O4: C, 63.71; H, 5.05; N, 12.38. Found: C, 63.60; H, 5.18; N, 12.29. 
15.	Compound 7f
IR (KBr): 3390, 3371, 2475, 2196, 1659, 1613 cm-1. 1H NMR (CDCl3 + DMSO-d6, 400 MHz): δ = 7.32 (d, J = 8.4 Hz, 2H), 7.06 (d, J = 8.4 Hz, 2H), 6.14 (s, 2H), 4.21 (s, 1H), 2.40 (s, 2H), 2.19-2.06 (m, 2H), 1.03 (s, 3H), 0.94 (s, 3H). ESI-MS m/z 373, 375 [M + H]+. Anal calcd for C18H17BrN2O2: C, 57.92; H, 4.59; N, 7.51. Found: C, 58.11; H, 4.37; N, 7.78. 
16.	Compound 7g
IR (KBr): 3390, 3317, 2300, 2190, 1659, 1606 cm-1. 1H NMR (CDCl3, 400 MHz): δ =7.06 (d, J = 8.4 Hz, 2H), 6.71 (brs, 2H), 4.43 (s, 2H), 4.26 (s, 1H), 2.86 (s, 6H), 2.36 (s, 2H), 2.15 (d, J = 3.6 Hz, 2H), 1.03 (s, 3H), 0.97 (s, 3H). ESI-MS m/z 338 [M + H]+. Anal calcd for C20H23N3O2: C, 71.19; H, 6.87; N, 12.45. Found: C, 71.14; H, 7.02; N, 12.33. 
17.	Compound 7h
IR (KBr): 3356, 2236, 2196, 1679, 1606 cm-1. 1H NMR (CDCl3, 400 MHz): δ = 7.20 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 8.4 Hz, 2H), 4.53 (s, 2H), 4.31 (s, 1H), 2.38 (s, 2H), 2.20-2.10 (m, 2H), 1.04 (s, 3H), 0.95 (s, 3H). ESI-MS m/z 329, 331 [M + H]+. Anal calcd for C18H17ClN2O2: C, 65.75; H, 5.21; N, 8.52. Found: C, 65.64; H, 5.23; N, 8.58. 
18.	Compound 7i
IR (KBr): 3390, 2350, 2190, 1672, 1639 cm-1. 1H NMR (CDCl3, 400 MHz): δ =7.54 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 8.0 Hz, 2H), 4.61 (s, 2H), 4.38 (s, 1H), 2.40 (s, 2H), 2.21-2.10 (m, 2H), 1.05 (s, 3H), 0.95 (s, 3H). ESI-MS m/z 320 [M + H]+. Anal calcd for C19H17N3O2: C, 71.46; H, 5.37; N, 13.16. Found: C, 71.65; H, 5.40; N, 13.37.


19.	Compound 7j 
IR (KBr): cm-1. 1H NMR (CDCl3, 400 MHz): δ = 7.26-7.05 (m, 4H), 4.78 (s, 1H), 4.56 (s, 2H), 2.38 (s, 2H), 2.19-2.05 (m, 2H), 1.04 (s, 3H), 0.99 (s, 3H). ESI-MS m/z 329, 331 [M + H]+. Anal calcd for C18H17ClN2O2: C, 65.75; H, 5.21; N, 8.52. Found: C, 65.57; H, 5.46; N, 8.45.
20.	Compound 7k
IR (KBr): 3317, 2380, 2183, 1659, 1593 cm-1. 1H NMR (CDCl3, 400 MHz): δ = 8.31(d, J = 8.4 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 8.4 Hz, 1H), 7.51 (t, J = 7.6 Hz, 1H), 7.42 (t, J = 7.4 Hz, 1H), 7.33 (t, J = 7.8 Hz, 1H), 7.17 (t, J = 7.2 Hz, 1H), 5.19 (s, 1H), 4.46 (s, 2H), 2.50-2.39 (m, 2H), 2.18-2.07 (m, 2H), 1.05 (s, 3H), 0.99 (s, 3H). ESI-MS m/z 345 [M + H]+. Anal calcd for C22H20N2O2: C, 76.72; H, 5.85; N, 8.13. Found: C, 76.64; H, 5.91; N, 7.96.
21.	Compound 7l

IR (KBr): 3310, 2909, 1719, 1679, 1613 cm-1. 1H NMR (DMSO-d6, 400 MHz): δ = 10.35 (s, 1H), 7.19 (s, 2H), 7.09-6.73 (m, 4H), 2.52 (m, 2H), 2.15 (d, J = 16.0 Hz, 1H), 2.06 (d, J = 16.0 Hz, 1H), 1.01 s, (3H), 0.98 (s, 3H). ESI-MS m/z 336 [M + H]+. Anal Calcd for: C19H17N3O3: C, 68.05; H, 5.11; N, 12.53. Found: C, 67.93; H, 5.26; N, 12.61.
22.	Compound 8a
IR (KBr): 3328, 2196, 1712, 1672, 1613 cm-1. 1H NMR (CDCl3 + DMSO-d6, 400 MHz): δ = 7.88-7.11 (m, 9H), 4.43 (s, 1H), 3.22 (brs, 2H). ESI-MS m/z 317 [M + H]+. Anal calcd for: C19H12N2O3: C, 72.15; H, 3.82; N, 8.86. Found: C, 72.04; H, 3.68; N, 8.80.
23.	Compound 8b
IR (KBr): 3396, 2203, 1712, 1606 cm-1. 1H NMR (CDCl3 + DMSO-d6, 400 MHz): δ = 7.85-6.99 (m, 8H), 4.40 (s, 1H), 3.20 (brs, 2H), 2.20 (s, 3H). ESI-MS m/z 331 [M + H]+. Anal calcd for: C20H14N2O3: C, 72.72; H, 4.27; N, 8.48. Found: C, 72.91; H, 4.36; N, 8.75
24.	Compound 8c
IR (KBr): 3476, 2196, 1719, 1613 cm-1. 1H NMR (CDCl3 + DMSO-d6, 400 MHz): δ = 8.07-7.23 (m, 8H), 4.60 (s, 1H), 3.11 (brs, 2H). 13C NMR (CDCl3 + DMSO-d6, 100 MHz): δ = 164.9, 163.3, 159.1, 157.3, 154.7, 151.7, 137.8, 133.7, 129.5, 128.5, 127.7, 123.6, 121.4, 117.7, 107.9, 62.5, 41.9. ESI-MS m/z 362 [M + H]+. Anal calcd for: C19H11N3O5: C, 63.16; H, 3.07; N, 11.63. Found: C, 62.87; H, 2.93; N, 11.54.
25.	Compound 8d
 IR (KBr): 3396, 2196, 1710, 1605 cm-1. 1H NMR (CDCl3 + DMSO-d6, 400 MHz): δ = 7.87-6.72 (m, 8H), 6.62 (brs, 2H), 4.42 (s, 1H), 3.69 (s, 3H). ESI-MS m/z 347 [M + H]+. Anal calcd for: C20H14N2O4: C, 69.36; H, 4.07; N, 8.09. Found: C, 69.55; H, 4.10; N, 8.30.
26.	Compound 8e
IR (KBr): 3421, 2201, 1712, 1614 cm-1. 1H NMR (CDCl3 + DMSO-d6, 400 MHz): δ = 7.89- 7.26 (m, 8H), 6.92 (brs, 2H), 4.56(s, 1H). ESI-MS m/z 342 [M + H]+. Anal calcd for: C20H11N3O3: C, 70.38; H, 3.25; N, 12.31. Found: C, 70.33; H, 3.37; N, 12.47.
27.	Compound 8f 
IR (KBr): 3317, 2203, 1712, 1533 cm-1. 1H NMR (DMSO-d6, 400 MHz): δ = 10.64 (s, 1H), 7.19 (d, J = 7.2 Hz, 1H), 7.74 (t, J = 7.0 Hz, 1H), 7.63 (brs, 2H), 7.52 (t, J = 7.6 Hz, 1H), 7.46 (d, J = 8.0 Hz, 1H), 7.19 (t, J = 6.8 Hz, 2H), 6.91 (t, J = 7.8 Hz, 1H), 6.82 (d, J = 8.0  Hz, 1H),. ESI-MS: m/z 358 [M + H]+. Anal Calcd for: C20H11N3O4: C, 67.23; H, 3.10; N, 11.76. Found: C, 67.12; H, 3.90; N, 11.66.











1.	Compound 6a 

1H NMR Spectra

















2.	Compound 6b 



1H NMR Spectra















3.	Compound 6b 

1H NMR Spectra




















4.	Compound 6c 

1H NMR Spectra
5.	Compound 6d 1H NMR Spectra
1H NMR Spectra


















6.	Compound 6d  13C NMR Spectra

13C NMR Spectra








7.	Compound 6e 

1H NMR Spectra

8.	Compound 6f 
1H NMR Spectra
9.	Compound6g
1H NMR Spectra


10.	Compound 6h 
1H NMR Spectra
11.	Compound 6i 
1H NMR Spectra




12.	Compound 7a 
1H NMR Spectra
13.	Compound 7a  
13C NMR Spectra

















14.	Compound 7b  

1H NMR Spectra
15.	Compound 7b  
13C NMR Spectra


16.	Compound 7c   
1H NMR Spectra
17.	Compound 7d  
1H NMR Spectra

18.	  Compound 7e  
1H NMR Spectra
19.	 Compound 7f  

1H NMR Spectra
20.	 Compound 7g  
1H NMR Spectra
21.	 Compound 7h  
1H NMR Spectra

22.	 Compound 7i  
1H NMR Spectra
23.	 Compound 7j  
1H NMR Spectra

24.	Compound 
7k 1H NMR Spectra

















25.	 Compound 7l  

1H NMR Spectra

















26.	Compound 8a   

1H NMR Spectra









27.	Compound 8b    

1H NMR Spectra
28.	Compound 8c    
1H NMR Spectra










29.	Compound 8c    

1H NMR Spectra
30.	Compound 8d    
1 H NMR Spectra














31.	Compound 8e    


1H NMR Spectra









32.	 Compound 8f    


1H NMR Spectra









1





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EtOAc-dispersed magnetic nanoparticles (DMNPs) of <i>γ</i>-Fe<sub>2</sub>O<sub>3</sub> in the single-pot domino preparation of 5-oxo-2-thioxo-3-thiophenecarboxylate derivatives

Erratum à l’article « Synthèse prébiotique dans les conditions hydrothermales » par Marie-Paule Bassez [C. R. Chimie 12 (6–7) (2009) 801–807]

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