CC BY ND NC 4.0 · SynOpen 2018; 02(02): 0150-0160
DOI: 10.1055/s-0036-1591960
paper
Copyright with the author

Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction

Mosim Amin Pathan
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502 285, India   Email: faiz@iith.ac.in
,
Faiz Ahmed Khan*
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502 285, India   Email: faiz@iith.ac.in
› Author Affiliations
F.A.K. gratefully acknowledges DBT for financial support. M.A.P. thanks CSIR for the award of a fellowship
Further Information

Publication History

Received: 15 January 2018

Accepted: 23 February 2018

Publication Date:
16 May 2018 (online)

Abstract

Pyrido-oxazine derivatives have been synthesized by employing tandem SN2 and SNAr reaction between 2,4,6-tribromo-3-(2-bromoethoxy)pyridine or 2,4,6-tribromo-3-(3-bromopropoxy)pyridine and a variety of primary amines. Moderate to good regioselectivity in favor of cyclization at the 2-position is observed. Pyrido-oxazine products thus generated are converted into biarylated pyrido-oxazine and terpyridine ligands.

Supporting Information

 
  • References

    • 1a Francisco W. Pivatto M. Danuello A. Regasini LO. Baccini LR. Young MC. M. Lopes NP. Lopes JL. C. Bolzani VS. J. Nat. Prod. 2012; 75: 408
    • 1b Fu P. Zhu Y. Mei X. Wang Y. Jia H. Zhang C. Zhu W. Org. Lett. 2014; 16: 4264
    • 1c Fu P. Liu P. Li X. Wang Y. Wang S. Hong K. Zhu W. Org. Lett. 2011; 13: 5948
    • 1d Qu X. Pang B. Zhang Z. Chen M. Wu Z. Zhao Q. Zhang Q. Wang Y. Liu Y. Wen L. J. Am. Chem. Soc. 2012; 134: 9038
    • 2a Kitanosono T. Zhu L. Liu C. Xu P. Kobayashi S. J. Am. Chem. Soc. 2015; 137: 15422
    • 2b Kawakami T. Murakami K. Itami K. J. Am. Chem. Soc. 2015; 137: 2460
    • 2c Jensen KL. Standley EA. Jamison TF. J. Am. Chem. Soc. 2014; 136: 11145
    • 2d Wendlandt AE. Stahl SS. J. Am. Chem. Soc. 2014; 136: 506
    • 2e Petersen AR. Taylor RA. Vicente-Hernández I. Mallender PR. Olley H. White AJ. P. Britovsek GJ. P. J. Am. Chem. Soc. 2014; 136: 14089
    • 3a Watterson SH. Chen P. Zhao Y. Gu HH. Dhar TG. M. Xiao Z. Ballentine SK. Shen Z. Fleener CA. Rouleau KA. Obermeier M. Yang Z. McIntyre KW. Shuster DJ. Witmer M. Dambach D. Chao S. Mathur A. Chen B.-C. Barrish JC. Robl JA. Townsend R. Iwanowicz EJ. J. Med. Chem. 2007; 50: 3730
    • 3b Wu W.-L. Burnett DA. Domalski M. Greenlee WJ. Li C. Bertorelli R. Fredduzzi S. Lozza G. Veltri A. Reggiani A. J. Med. Chem. 2007; 50: 5550
    • 3c Perry B. Alexander R. Bennett G. Buckley G. Ceska T. Crabbe T. Dale V. Gowers L. Horsley H. James L. Jenkins K. Crépy K. Kulisa C. Lightfoot H. Lock C. Mack S. Morgan T. Nicolas A.-L. Pitt W. Sabin V. Wright S. Bioorg. Med. Chem. Lett. 2008; 18: 4700
    • 3d Hinman MM. Rosenberg TA. Balli D. Black-Schaefer C. Chovan LE. Kalvin D. Merta PJ. Nilius AM. Pratt SD. Soni NB. Wagenaar FL. Weitzberg M. Wagner R. Beutel BA. J. Med. Chem. 2006; 49: 4842
    • 4a Kazuhisa I. Toshiaki N. Mika M. Tomomi I. Tetrahedron 2015; 71: 407
    • 4b Taisuke K. Yoshihide T. Tetsuya T. Yoshihisa N. Tetrahedron Lett. 2015; 56: 6043
    • 4c Vadim B.-G. Arturo A. Antonio A. Mehdi B. Robert H. Alexey K. Pedro R.-N. Alexander T. Ralf S. ACS Chem. Neurosci. 2015; 6: 260
    • 4d Haoran S. Stephen GD. Angew. Chem. Int. Ed. 2006; 45: 2720
    • 4e Carla B. Thierry R. Manfred S. Chem. Eur. J. 2005; 11: 1903
    • 4f Mark P. Simon C. Edward M. Julian B. Tetrahedron 2010; 66: 2398
    • 4g Anita T. William RW. Robert FS. Bioorg. Med. Chem. 2002; 10: 3593
    • 4h Joydev KL. Gregory DC. Synthesis 2008; 4002
    • 5a Kim JG. Yang EH. Youn WS. Choi JW. Ha D.-C. Ha JD. Tetrahedron Lett. 2010; 51: 3886
    • 5b Brooks G. Dabbs S. Davies DT. Hennessy AJ. Jones GE. Markwell RE. Miles TJ. Owston NA. Pearson ND. Peng TW. Tetrahedron Lett. 2010; 51: 5035
    • 5c Isabelle T. Carsten B. Org. Lett. 2012; 14: 1892
    • 5d Graham S. Rachel S. Dmitrii SY. Judith AK. H. Antonio V. J. Fluorine Chem. 2014; 167: 91
    • 6a Sharifi A. Barazandeh M. Abaee MS. Mirzaei M. Tetrahedron Lett. 2010; 51: 1852
    • 6b Ramesh C. Raju BR. Kavala V. Kuo C.-W. Yao C.-F. Tetrahedron 2011; 67: 1187
    • 6c Dai W.-M. Wang X. Ma C. Tetrahedron 2005; 61: 6879
    • 6d Bower JF. Szeto P. Gallagher T. Org. Lett. 2007; 9: 3283
    • 6e Arrault A. Touzeau F. Guillaumet G. Léger J.-M. Jarry C. Mérour J.-Y. Tetrahedron 2002; 58: 8145
    • 6f Hartz RA. Nanda KK. Ingalls CL. Tetrahedron Lett. 2005; 46: 1683
    • 6g Henry N. Guillaumet G. Pujol MD. Tetrahedron Lett. 2004; 45: 1465
    • 7a Khan FA. Ahmad S. J. Org. Chem. 2012; 77: 2389
    • 7b Khan FA. Ahmad S. Tetrahedron Lett. 2013; 54: 2996
    • 7c Khan FA. Ahmad S. Kodipelli N. Shivange G. Anindya R. Org. Biomol. Chem. 2014; 12: 3847
  • 8 Pathan MA. Khan FA. Tetrahedron 2017; 6008