6474
M. Poornachandran, R. Raghunathan / Tetrahedron 64 (2008) 6461–6474
70 eV): m/z, 424.30 (Mþ). Anal. Calcd for C20H21N2O2S2Cl: C, 57.06;
H, 5.03; N, 6.65%. Found: C, 57.14; H, 5.10; N, 6.58%.
12. (a) Grigg, R.; Surendrakumar, S.; Thianpatanagul, S.; Vipond, D. J. Chem. Soc.,
Perkin Trans. 11988, 2693–2701; (b) Grigg, R.; Idle, J.; McMeekin, P.; Vipond, D. J.
Chem. Soc., Perkin Trans. 1 1988, 2703–2714; (c) Tsuge, O.; Kanemasa, S. Adv.
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(e) Novikov, M. S.; Khlebnikov, A. F.; Besidina, O. V.; Kastikov, R. R. Tetrahedron
Lett. 2001, 42, 533–535.
4.12.11. cis-2-(p-Bromo)-phenyl-6-N-benzenesulfonylper-
hydrothiazolo[30,40-2,3]pyrrolo[4,5-c]pyrrole 32e
Colorless solid, 69% (0.323 g); mp: 129–131 ꢀC; IR (KBr): 1338
and 1166 cmꢁ1 1H NMR (CDCl3, 400 MHz):
; d 2.00–2.13 (m, 2H),
2.54–2.63 (m, 1H), 2.85–2.99 (m, 4H), 3.08–3.23 (m, 3H), 3.41–3.70
(dt, 1H, J1¼2.5 Hz, J2¼9.3 Hz), 5.39 (s, 1H), 7.16–7.71 (m, 9H, Ar–H);
14. (a) Padwa, A. Angew. Chem., Int. Ed. Engl. 1976, 15, 123–180; (b) Oppolzer. Angew.
Chem., Int. Ed. Engl. 1977, 16, 10–23.
13C NMR (CDCl3, 100 MHz):
d 34.8, 38.5, 41.4, 53.4, 54.9, 67.3, 69.0,
15. Jacobi, P. A.; Martinelli, M. J.; Polane, S. J. Am. Chem. Soc. 1984, 106, 5594–5598.
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P. N.; Huie, E. M. J. Am. Chem. Soc. 1984, 106, 7175–7178; (c) Mahmud, H.; Lovely,
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19. (a) Poornachandran, M.; Raghunathan, R. Tetrahedron 2006, 62, 11274–11281;
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2002, 32, 3587–3594; (e) Amalraj, A.; Raghunathan, R. Tetrahedron 2001, 57,
10293–10298; (f) Subramaniyan, G.; Raghunathan, R.; Nethaji, M. Tetrahedron
2002, 58, 9075–9079.
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21. See Ref. 16c.
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A.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
120.9, 127.7, 128.3, 129.6, 131.1, 132.7, 142.2, and 143.5. Mass spec-
trum (EI, 70 eV): m/z, 468.12 (Mþ). Anal. Calcd for C20H21N2O2S2Br:
C, 51.61; H, 4.55; N, 6.02%. Found: C, 51.57; H, 4.61; N, 5.93%.
4.12.12. cis-2-(p-Fluoro)-phenyl-6-N-benzenesulfonylper-
hydrothiazolo[30,40-2,3]pyrrolo[4,5-c]pyrrole 32f
Pale brown solid, 72% (0.291 g); mp: 135–137 ꢀC; IR (KBr): 1340
and 1166 cmꢁ1 1H NMR (CDCl3, 400 MHz):
; d 1.99–2.12 (m, 2H),
2.57–2.61 (m, 1H), 2.86–2.88 (m, 1H), 2.95–2.99 (m, 1H), 3.10–3.26
(m, 3H), 3.41–3.50 (m, 2H), 3.67–3.69 (dt, 1H, J1¼2.5 Hz, J2¼9.4 Hz),
5.40 (s, 1H), 6.89–7.83 (m, 9H, Ar–H); 13C NMR (CDCl3, 100 MHz):
d
30.9, 34.9, 38.7, 41.1, 53.6, 54.7, 67.3, 68.9, 114.7, 114.9, 127.7, 128.3,
128.3, 129.0, 132.7, 135.7, 138.8, 160.6, and 163.0. Mass spectrum (EI,
70 eV): m/z, 404.52 (Mþ). Anal. Calcd for C20H21N2O2S2F: C, 59.38;
H, 5.23; N, 6.93%. Found: C, 59.30; H, 5.32; N, 6.84%.
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Acknowledgements
The authors thank Department of Science and Technology (DST),
New Delhi, India for financial support. One of the authors M.P.
thanks Council of Scientific and Industrial Research (CSIR), New
Delhi, for the financial support as the award of Senior Research
Fellowship (SRF).
Raghunathan, R. Acta Crystallogr. 2005, E61, o2493–o2495.
28. Pedrosa, R.; Andre´s, C.; Nieto, J.; Pe´rez-Cuadrado, C.; San Francisco, I. Eur. J. Org.
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