H. S. P. Rao, K. Geetha / Tetrahedron Letters 50 (2009) 3836–3839
3839
Table 4
References and notes
Synthesis of 3-nitro-4H-chromenes 6a–e from high boiling thiols 5a–e
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SMe
SR
EtOH
reflux
NO2
NO2
RSH
+
9-18 h
75-93%
O
NHMe
O
NHMe
3a
5a-e
6a-e
3. Moder, K. P. Eur. Pat. Appl. EP 515121 A1, 1992; Chem. Abstr. 1993, 118, 169100.
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Entry
Thiol (RSH)
Product
Time (h)
Yield (%)
1
2
3
4
5
5a: R = C6H5
6a: R = C6H5
12
12
12
18
19
90
80
75
91
93
5b: R = 4-CH3C6H5
5c: R = 4-ClC6H5
5d: R = CH3(CH2)3
5e: R = CH3(CH2)7
6b: R = 4-CH3C6H5
6c: R = 4-ClC6H5
6d: R = CH3(CH2)3
6e: R = CH3(CH2)7
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in 3a could be replaced with long chain/aryl thiols.
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S.; Carosati, E.; Sanchez, L. C.; Baroni, M.; Mannhold, R. Bioorg. Med. Chem. 2007,
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Markopoulos, J.; Markopoulou, O. I. Bioorg. Med. Chem. 2006, 14, 6686–6694;
(h) Doshi, J. M.; Tian, D.; Xing, C. J. Med. Chem. 2006, 49, 7731–7739.
8. Rao, H. S. P.; Geetha, K. Deposited with Cambridge Crystallographic Data
Center, CCDC; deposition No. 261071.
Acknowledgements
H.S.P.R. thanks UGC, UGC-SAP, CSIR and DST-FIST for financial
assistance. K.G. thanks CSIR for awarding SRF. We thank IACS, Kolk-
ata, and SAIC, IIT, Chennai, for recording spectra. We thank Shasun
Chemicals and Drugs Ltd, Chennai, for generous gift of NMSM.
Supplementary data
9. Gayathri, D.; Velmurugan, D.; Ravikumar, K.; Geetha, K.; Rao, H. S. P. Acta
Crystallogr., Sect. E 2006, 62, o1961–o1963.
10. Bhaskaran, S.; Velmurugan, D.; Ravikumar, K.; Geetha, K.; Rao, H. S. P. Acta
Crystallogr., Sect. E 2006, 62, o188–o190.
Supplementary data associated with this article can be found, in