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Organic & Biomolecular Chemistry
Page 6 of 7
ARTICLE
Journal Name
4.
5.
100−200 mesh size silica gels (hexane: ethyl acetate) to afford
the corresponding product. The structure and purity of known
starting materials 1p, 1q, 1t, 1u were confirmed by comparison
of their physical and NMR-spectral data (1H NMR and 13C NMR)
with those reported in the literature.18-21
3568−3572; (b) A. Gangjee, Y. Zeng, T. Talreja, J. J.
McGuire, R. L. Kisliuk, S. F. Queener and J. Med. Chem.,
2007, 50, 3046–305.
(a) J. Matysiak, Bioorg. Med. Chem., 2006, 14, 2613–2619;
Acc. Chem. Res., 2013, 46, 519–528; (c) K. Scherlach, H.
W. Ntzmann, V. Schroeckh, H.-M. Dahse, A. A. Brakhage
and C. Hertweck, Angew. Chem. Int. Ed., 2011, 50, 9843 –
9847.
(a) N. Yongpruksa, S. Pandey, G. A. Baker and M. Harmata,
Org. Biomol. Chem., 2011, 9, 7979–7982; (b) M. Harmata,
687; (b) T. S. Jiang, X. G. Zhang and J. H. Li, Synthesis 2009,
18, 3029–3038; (c) R. M. Gai, R. F. Schumacher, D. F. Back
and G. Zen, Org. Lett., 2012, 14, 6072–6075.
General experimental procedure for green one-pot
synthesis of benzo[1,3]thiazin-2-yl)benzimidic acid 3-5: To a
solution of ortho-alkynlanilines
1
(0.5 mmol), aroy
lisothiocyanates 2 (0.52 mmol) and 2.0 equiv of I2 was added in
water (2.0 mL). The reaction was then stirred at room
temperature until TLC revealed a complete conversion of the
starting material. After the completion of the reaction, the
reaction mixture was quenched with saturated aq sodium
thiosulfate solution and extracted with EtOAc (3X10 mL). The
combined organic layers were dried over Na2SO4, concentrated
under vacuum, and purified by column chromatography using
100−200 mesh size silica gels (EtOAc: hexane) to afford the
corresponding product.
6.
7.
General experimental procedure for green one-pot
synthesis of Bisbenzo[1,3]thiazin-2-yl)di benzimidic acid 7: To
a
solution of ortho-haloanilines
1
(0.5 mmol),
aroylisothiocyanates 2 (1.04 mmol) and 3.5 equiv of I2 were
added in water (2.0 mL). The reaction was then stirred at room
temperature until TLC revealed complete conversion of the
starting material. After the completion of the reaction, the
reaction mixture was quenched with saturated aq sodium
thiosulfate solution and extracted with EtOAc (3X10 mL). The
combined organic layers were dried over Na2SO4, concentrated
under vacuum, and purified by column chromatography using
100−200 mesh size silica gels (EtOAc:hexane) to afford the
corresponding product.
8.
9.
A. R. Katritzky, Y. J. Xu and R. Jain, J. Org. Chem., 2002, 67,
8234–8236.
Q. Ding and J. Wu, J. Comb. Chem., 2008, 10, 541–545.
271.
Lett., 2009, 11, 2776–2779.
12. R. K. Saunthwal, M. Patel, S. Kumar and A. K. Verma,
Tetrahedron Lett., 2015, 56, 677–681.
13. H. Sashida, M. Kaname, M. Minoura, Tetrahedron,
2013,69, 6478–6487.
14. R. K. Saunthwal, M. Patel, R. K. Tiwari, K. Parang and A. K.
Verma, Green Chem. 2015, 17, 1434–1441.
15. A. Modi, P. Sau and B. K. Patel, Org. Lett., 2017, 19, 6128–
6131.
Conflicts of interest
There are no conflicts of interest to declare.
16. (a) S. P. Shukla, J. Singh and V. Rustagi, J. Org. Chem.
7703; (c) A. K. Verma, T. Aggarwal, V. Rustagi and R. C.
Larock, Chem. Commun., 2010, 46, 4064–4066; (d) R. K.
Saunthwal, A. K. Danodia, M. Patel, S. Kumar and A. K.
Verma, Chem. Asian J., 2016, 11, 3001–3007; (e) H. H.
Zhang, Y. Q. Wang, L. T. Huang, L. Q. Zhu, Y. Y. Feng, Y.
M. Lu, Q. Y. Zhao, X. Q. Wang, Z. Wang, Chem. Commun.,
2018, 54, 8265–8268; (f) Y. Jiang, J. X. Zou, L. T. Huang, X.
Peng, J. D. Deng, L. Q. Zhu, Y. H. Yang, Y. Y. Feng, X. Y.
Zhang, Z. Wang,Org. Biomol. Chem., 2018, 16, 1641–1645.
17. Crystallographic data for the compound 4h has been
deposited with the Cambridge Crystallographic Data
Centre. CCDC deposit number for compound 4h is
1872209, contains all crystallographic details of this
publication and is available free of charge at
Acknowledgements
We gratefully acknowledge the SERB for financial support and
USIC, the University of Delhi for providing instrumentation
facilities. K.M.S. and S.K. are thankful to CSIR for fellowship.
Notes and references
1.
T. Aggarwal, S. Kumar and A. K. Verma, Org. Biomol.
Chem., 2016, 14, 7639–7653.
2.
(a) F. Yang, T. Jin, M. Baoc and Y. Yamamoto, Chem.
Commun., 2011, 47, 4541–4543; (b) Y. X. Xie, X. Y. Liu, L. Y.
Wu, Y. Han, L. B. Zhao, M. J. Fan and Y. M. Liang, Eur. J.
1134–1139.
3.
R. Hull, M. P. J. van den Broek, M. L. Swain and J. Chem.
Soc., Perkin Trans.1, 1975, 922–925.
6 | J. Name., 2012, 00, 1-3
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