Synthesis of spiro[pyrrole-2,5′-pyrrolo[2,3-d]pyrimidines] by reaction of pyrrolobenzoxazinetriones with 6-aminouracil

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

3-Aroylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones react with 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione with formation of 3-aroyl-4-hydroxy-1-(2-hydroxyaryl)-1′,3′-dimethylspiro[pyrrole-2,5′-pyrrolo[2,3-d]-pyrimidine]-2′,4′,5,6′ (1H,1′H,3′H,7′H)-tetraons, the structure of which was confirmed by X-ray diffraction analysis. A simple method for constructing a hard-to-reach heterocyclic system of spiro[pyrrole-2,5′-pyrrolo[2,3-d]-pyrimidine] is described.

About the authors

A. I. Kobelev

Perm State University

Email: koh2@psu.ru
ORCID iD: 0000-0001-8606-7908
Russian Federation, ul. Bukireva, 15, Perm, 614990

M. V. Dmitriev

Perm State University

Email: koh2@psu.ru
ORCID iD: 0000-0002-8817-0543
Russian Federation, ul. Bukireva, 15, Perm, 614990

A. N. Maslivets

Perm State University

Author for correspondence.
Email: koh2@psu.ru
ORCID iD: 0000-0001-7148-4450
Russian Federation, ul. Bukireva, 15, Perm, 614990

References

  1. Ghahremanzadeh R., Azimi S.C., Gholami N., Bazgir A., Chem. Pharm. Bull., 2008, 56, 1617–1620. doi: 10.1248/cpb.56.1617
  2. Ohshita K., Ishiyama H., Oyanagi K., Nakata H., Kobayashi J.I. Bioorg. Med. Chem., 2007. 15, 3235–3240. doi: 10.1016/j.bmc.2007.02.043
  3. Stefanachi A., Nicolotti O., Leonetti F., Cellamare S., Campagna F., Loza M. I., Brea J.M., Mazza F., Gavuzzo E., Carotti A. Bioorg. Med. Chem., 2008, 16, 9780–9789. doi: 10.1016/j.bmc.2008.09.067
  4. Cheng F., Xu Z., Liu G., Tang, Y. Eur. J. Med. Chem., 2010, 45, 3459–3471. doi: 10.1016/j.ejmech.2010.04.039
  5. Gill C.H., Chate A.V., Shinde G.Y., Sarkate A.P., Tiwari S.V. Res. Chem. Intermed., 2018, 44, 4029–4043. doi: 10.1007/s11164–018–3353–9
  6. Третьяков Н.А., Дмитриев М.В., Масливец А.Н. ЖОрХ. 2023, 59, 180–186. [Tretyakov N.A., Dmitriev M.V., Maslivets A.N. Russ. J. Org. Chem, 2023, 59, 237–242.] doi: 10.1134/S1070428023020033
  7. Spek A.L. Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71, 9–18. doi: 10.1107/S2053229614024929
  8. Масливец А.Н., Машевская И.В., Смирнова Л.И., Красных О.П., Шуров С.Н., Андрейчиков Ю.С. ЖОрХ, 1992, 28, 2545–2553. [Maslivets A.N., Mashevskaya I.V, Krasnykh O.P., Shurov S.N., Andreichikov Yu.S. J. Org. Chem. USSR 1992, 28, 2056-2062.]
  9. CrysAlisPro, Agilent Technologies, Version 1.171.37.33.
  10. Sheldrick G.M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112–122. doi: 10.1107/S0108767307043930
  11. Sheldrick G.M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71, 3–8. doi: 10.1107/S2053229614024218
  12. Dolomanov O.V., Bourhis L.J., Gildea R.J, Howard J.A.K., Puschmann H. J. Appl. Cryst. 2009, 42, 339–341. doi: 10.1107/S0021889808042726

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2024 Russian Academy of Sciences