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Organic & Biomolecular Chemistry
Page 4 of 4
COMMUNICATION
Journal Name
Initially, 1a condensed with 2a to afford thiourea intermediate Chem. Commun. 2017, 8, 1069. c) A. N. Panday, E.VMiew. AVrtiilcllae,OEn.linJe.
A. Next, intermediate A reacts with NH4OAc to give imine
intermediate B, followed by intramolecular attack of the imine
DOI: 10.1039/C9OB00349E
North. Tetrahedron Lett. 2017, 58, 1276.
NH group onto the thiocarbonyl carbon with concomitant 7 Y. Wang, H. Wang, J. Pent, Q. Zhu. Org. Lett. 2011, 13, 4604.
trapping of the S anion to afford the cyclised product C.
Intermediate C on aromatization affords 3a with subsequently
8 L. Q. Tran, J. Li. Neuville. J. Org. Chem. 2015, 80, 6102.
generation of S and HI. Similarly, when 1a condensed with 4a 9 R. S. Pathare, M. K. Mayura, A. Kumari, V. K. Agnihotri, V. P,
gives thiourea intermediate D which leads to the formation of
cyclised E via N-C and S-I bond formation. Upon aromatization
Verma, D. M. Sawant. Org. Biomol. Chem. 2019, 17, 363.
of E with the generation of HI and S affords the desired product 10 P. P. Renaut, P. Durand, Ratel. Synthesis. 2000, 14, 2009.
5a.
11 (a) J. Zhang, X. Wu, Q. Gao, X. Geng, P. Zhao, D. Y. Wu, A. Wu.
Conclusions
Org. Lett. 2017, 19, 408. (b) H. Cui, X. Liu, D. Yang, C. He. T. Zhang,
In summary, we have developed a new strategy for the
constructing of N,4-disubstituted quinazolin-2-amine/4-aryl-2-
(arylamino)quinazoline- 3-oxide from isothiocyanate, 2-amino
H. Wang. J. Org. Chem. 2016, 81, 2252. c) Z. Lv, J. Liu, W. Wei, J.
Wu, W. Yu, J. Chang. Adv. Synth. Catal. 2016, 358, 2759. (d) N.
benzophenone and (2-aminophenyl)(phenyl)methanone oxime
under iodine catalysis. This methodology possesses several
advantages, such as metal free protocol, the use of molecular
iodine and readily available isothioctanates, 2-amino
benzophenones and ammonium acetates. We believe that this
methodology will find useful application for the synthesis of
valuable quinazolines/quinazoline oxides in economical
manner.
Tumula, N. Jatangi, R. K. Palakodety, S. Balasubramanian, M.
Nakka. J. Org. Chem. 2017, 82, 5310.
12 N. Jatangi, N. Tumula,; R. K. Palakodety, M. Nakka. J. Org
.Chem. 2018, 83, 5715.
13 (a) D. Zhao, Q. Shen, J. L. Xin. Adv. Synth. Catal. 2015, 357, 339.
(b) A. Kamal, K. Suresh babu, C. Chandrasekhar, B. Nagaraju, K. N.
Visweswara sastry, C. Ganesh kumar, Tetrahedron Lett. 2015, 56,
6373.
Conflicts of interest
14 C. M. Counceller, C. C. Eichman, B. C. Wray, J. P. Stambuil, Org.
Lett. 2008, 10, 1021.
“There are no conflicts to declare”.
Acknowledgements
The author J. N thank the UGC, New Delhi for financial support
in the form of fellowships.
15 (a) R. Alonso, A. Caballero, P. J. Campos, D. Sampedro, M. A.
Rodriguez. Tetraheron. 2010, 66, 4469. (b) F. Portela-cubillo, J. S.
Scott, J. C. Walton. J. Org. Chem. 2009, 74, 4934.
16 S. Jiao, Z. Wang, Q. Zhao, W. Yu, J. Chang. Tetraheron. 2018,
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Notes and references
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4 | J. Name., 2012, 00, 1-3
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