N. J. Parmar et al. / Bioorg. Med. Chem. Lett. 22 (2012) 4075–4079
4079
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52, 2853; (b) Parmar, N. J.; Patel, R. A.; Teraiya, S. B.; Sharma, D.; Gupta, V. K.
RSC Adv. 2012, 2, 3069 DOI:10.1039/C2RA00930G.(In Press).
this has been set and it will be efficiently developed to assess new
bioprofiles.
9. Rosini, M.; Budriesi, R.; Bixel, M. G.; Bolognesi, M. L.; Chiarini, A.; Hucho, F.;
Krogsgaard-Larsen, P.; Mellor, A.; Minarini, A.; Tumiatti, V.; Usherwood, P. N.
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Acknowledgments
10. Shadomy, S.; Pfaller, M. A.; Laboratory Studies with Antifungal Agents:
Susceptibility Tests and Quantitation in Body Fluids. In Manual of Clinical
Microbiology, 5th ed.; Balows, A.; Hausler, W. J.; Hermann, K. L.; Isenberg, H.
D.; Shadomy, H. J. Eds.; Washington DC, 1991; Chapter 117, p 1173.
11. National Committee for Clinical Laboratory Standards. Methods for
Dilutionantimicrobial Susceptibility Tests for Bacteria that Grow Aerobically,
5th ed.; Approved Standard (M7A5); National Committee for Clinical
Laboratory Standards: Wayne, PA, 2000.
We sincerely express our thanks to the Head, Department of
Chemistry, S. P. University for providing necessary research facili-
ties. Two authors (B.R.P, H.A.B.) acknowledge financial supports
from the UGC under the UGC RFSMS Scheme, and one author
(Rajnikant) acknowledges the DST, New Delhi for National Facility
of a single crystal X-ray diffractometer under Project No. SR/S2/
CMP-47/2003. We also acknowledge the help rendered by the
Vaibhav Analytical Laboratories, Ahmadabad and Nutan Dye Chem,
Surat.
12. Synthesis of aryldiazenylhexahydrochromeno [4,3-b] pyrroles 3a–3m: A mixture
of an aldyhyde 1 (0.5 g, 1.88 mmol) and an amine 2 (1 equiv) was heated in a
round bottom flask equipped with preheated air condenser from 0.75 to 2.5 h.
After confirming the completion of reaction by TLC, it was cooled to room
temperature. The resulted reaction mass was passed through silica bed column
to get pure product. The same reaction was performed under microwave
irradiation at 280 W for 10 min. Compound 3a: yellow Solid, yield 90%, 0.746 g,
Supplementary data
mp 104–106 °C; IR (m
max, cmꢀ1): 3081, 3022, 2950,1724 (C=O), 1681, 1575,
1493, 1244, 1032, 852, 768, 749, 690; 1H NMR (400 MHz, CDCl3): d 1.29 (t,
3J = 7.2 Hz, 3 H, OCH2CH3), 1.95 (ddd, 2J3’,3 = 11.6, 3J3’,2 = 8.6, 3J3’,3a = 3.2 Hz, 1 H,
H-30), 2.20 (ddd, 2J3,3’ = 10.2, 3J3,3a = 8.4, 3J3,2 = 3.6 Hz, 1 H, H-3), 2.68 (m, 1 H, H-
3a), 3.62 (dd, 3J2,3’ = 9.0, 3J2,3 = 3.2 Hz, 1 H, H-2), 3.91 (d, 2J = 13.2 Hz, 1 H, one of
NCH2Ph), 4.18 (m, 2 H of H-4 and 2 H of OCH2CH3), 4.35 (d, 2J = 13.2, 1 H, the
Supplementary data associated with this article can be found, in
3
other of NCH2Ph),,4.44 (d, J9b,3a = 5.6 Hz, 1 H, H-9b) 7.0–7.93 (m, 13 H, Ar-H);
13C NMR (100 MHz, CDCl3): d 14.27 (OCH2CH3), 29.99 (C-3), 34.45 (C-3a), 51.22
(NCH2Ph), 57.92 (C-2), 59.45 (C-9b), 60.48 (OCH2CH3), 67.86 (C-4), 117.92,
122.57, 122.84, 123.46, 127.23, 128.22, 128.76, 129.03, 129.38, 130.34, 138.91,
146.45, 152.81, 158.32 (arom.), 173.78 (C=O); ESI-MS: m/z: 442.2 (M+H)+,Anal
Calcd for C27H27N3O3: C, 73.45; H, 6.16; N, 9.52. Found: C, 73.08; H, 6.46; N,
9.27.
References and notes
1. (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57,
9225; (b) Nagariya, A. K.; Meena, A. K.; Kiran; Yadav, A. K.; Niranjan, U. S.;
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´
Dıaz-Ortiz, A.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164; (d) Kappe, Oliver. C
13. Synthesis of (2R,3aS,9bR)-ethyl-8-amino-1-benzyl-1,2,3,3a,4,9b-hexahydrochro-
Angew. Chem., Int. Ed. 2004, 43, 6250.
meno [4,3-b]pyrrole-2-carboxylate 4a:
A solution of diazenylcompound 3a
2. (a) Novikov, M. S.; Khlebnikov, A. F.; Shevchenko, M. V.; Kostikov, R. R.; Vidovic,
D. Russ. J. Org. Chem. 2005, 41, 1496; (b) Ruano, J. L. G.; Tito, A.; Peromingo, M. T.
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Chem. 2002, 37, 953; (d) Periyasami, G.; Raghunathan, R.; Surendiran, G.;
Mathivanan, N. Bioorg. Med. Chem. Lett. 2008, 18, 2342.
(0.5 g, 1.87 mmol), prepared in 20 ml hot concentrated HCl, was added drop
wise a solution of 2 g tin (ll) chloride in 5 ml same acid until it decolorized the
resulted reaction mass. It was then cooled and added 10% sodium hydroxide
solution until tin hydroxide precipitates redissolved. Four 20 ml ether extracts
of this cold solution were combined and dried with anhydrous sodium
sulphate followed by ether evaporation. A crude amino derivative obtained as a
residue, was then purified by column chromatography. Compound 4a: Brown
´
3. (a) Llamas, T.; Arrayas, R. G.; Carretero, J. C. Org. Lett. 2006, 8, 1795; (b) Stanley,
L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887; (c) Pandey, G.; Banerjee, P.; Gadre,
S. R. Chem. Rev. 2006, 106, 4484; (d) Le0vesque, F.; Be0langer, G. Org. Lett. 2008,
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Solid, yield 62%, 0.247 g, mp = 88–90 °C IR (m
max, cmꢀ1): 3432, 3205, 3018,
2946, 1732 (C=O), 1608, 1535, 1491, 1214, 1020, 822, 761, 749, 689; 1H NMR
4. (a) Coldham, I.; Dobson, B. C.; Franklin, A. I.; Fletcher, S. R. Tetrahedron Lett.
2007, 48, 873; (b) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron
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1125.
5. (a) Barnéoud, P.; Mazadier, M.; Miquet, J. M.; Parmentier, S.; Dubédat, P.; Doble,
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6. aPhotochromism: Molecules and Systems; Bouas-Laurent, H., Ed.; Elsevier:
Amsterdam, 1990; bOrganic Photochromic and Thermochromic Compounds;
Crano, J. C., Guglielmetti, R. J., Eds.; Kluwer Academic/Plenum Publishers:
New York, 1999. 1 and 2.
(400 MHz, DMSO-d6): d 1.16 (t, 3J = 7.2 Hz, 3 H, OCH2CH3), 1.87 (ddd, 2J3’,3 = 7.2,
3
2
3
3J3’,2 = 5.0, J3’,3a = 4.0 Hz,
1
H, H-30), 2.00 (ddd, J3,3’ = 11.6, J3,3a = 9.2,
3J3,2 = 3.2 Hz, 1 H, H-3), 2.70 (m, 1 H, H-3a), 3.40 (dd, J2,3’ = 8.8, J2,3 = 3.2 Hz,
3 3
1 H, H-2), 3.69 (d, 2J = 13.6 Hz, 1 H, one of NCH2Ph), 3.81 (dd, J4,4 = 18.2,
2
3J4,3a = 10.4 Hz, 1 H, one of H-4), 3.86 (dd, J4,4 = 10.8, J4,3a = 4.8 Hz, 1 H, the
other of H-4), 4.06 (m, 1 H, H-9b and 2 H of OCH2CH3), 4.19 (d, 3J9b,3a = 13.6 Hz,
1 H, the other of NCH2Ph), 4.65 (s, 2 H, NH2), 7.45–7.27 (m, 8 H, Ar-H); 13C NMR
(100 MHz, DMSO-d6): d 14.63 (OCH2CH3), 30.21 (C-3), 35.25 (C-3a), 51.22
(NCH2Ph), 58.21 (C-2), 59.55 (C-9b), 60.18 (OCH2CH3), 67.70 (C-4), 115.57,
117.19, 117.29, 122.61, 127.32, 128.45, 128.64, 139.39, 142.10, 146.93, (arom.),
173.85 (C=O); ESI-MS: m/z: 352.8 (M+H)+, Anal Calcd C21H24N2O3: C, 71.57; H,
6.86; N, 7.95. Found: C, 71.46; H, 6.98; N, 8.02.
2
3
7. Mannhold, R.; Cruciani, G.; Weber, H. J. Med. Chem. 1999, 42, 981.