Synthesis of Spiro[indole-3,2′-pyrrole]triones by the Reaction of Pyrrolobenzoxazepinetriones with Enaminoketone

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

The reaction of 3-aroylpyrrolo[1,2-a][4,1]benzoxazepin-1,2,4-triones with 3-cyclohexylamino-5,5-dimethylcyclohex-2-en-1-one leads to the formation of 3′-(4-aroyl)-4′-hydroxy-1′-(2-(hydroxymethyl)phenyl)-6,6-dimethyl-1-cyclohexyl-6,7-dihydrospiro[indole-3,2′-pyrrole]-2,4,5′(1H,1′H,5H)-triones. A new scheme for the interaction of 3-aroylpyrrolo[1,2-а][4,1]benzoxazepine-1,2,4-triones with N-substituted enaminoketones leading to the formation of derivatives of the difficult-to-reach heterocyclic systems of spiro[indole-3,2′-pyrrole]triones is described.

Full Text

Restricted Access

About the authors

A. A. Maslivets

Perm State University

Email: koh2@psu.ru
ORCID iD: 0000-0003-0555-0231
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. Масливец А.А., Масливец А.Н. ЖОрХ. 2015, 51, 1213-1214. [Maslivets A.A., Maslivets A.N. Russ. J. Org. Chem. 2015, 51, 1194–1195.] doi: 10.1134/S1070428015080254
  2. Машевская И.В., Дувалов А.В., Толмачева И.А., Алиев З.Г., Масливец А.Н. ЖОрХ. 2004, 40 (9), 1359–1363. [Mashevskaya, I.V., Duvalov, A.V., Tolmacheva, I.A., Aliev Z. G., Maslivets A. N. Russ J Org Chem. 2004, 40, 1359–1363.] doi: 10.1007/s11178-005-0020-6
  3. Zhao J.Q., Zhou X.J., Zhou Y., Xu X.Y., Zhang X.M., Yuan W.C. Org. Lett. 2018, 20, 909–912. doi: 10.1021/acs.orglett.7b03667
  4. Han Y., Wu Q., Sun J., Yan C.G. Tetrahedron. 2012, 68, 8539–8544. doi: 10.1016/j.tet.2012.08.030.
  5. Sarkar R., Mukhopadhyay C. Tetrahedron Lett. 2013, 54, 3706–3711. doi: 10.1016/j.tetlet.2013.05.017
  6. Dou P.H., Chen Y., You Y., Wang Z.H., Zhao J.Q., Zhou M.Q., Yuan W.C. Adv. Synth, Catal. 2021, 363, 4047–4053. doi: 10.1002/adsc.202100516
  7. Srivastava A., Mobin S.M., Samanta S. Tetrahedron Lett. 2014, 55, 1863–1867. doi: 10.1016/j.tetlet.2014.01.154
  8. CrysAlisPro, Agilent Technologies, Version 1.171.37.33.
  9. Sheldrick G.M. ActaCryst. 2008, A64, 112–122. doi: 10.1107/S0108767307043930
  10. Sheldrick G.M. ActaCryst. 2015, C71, 3–8. doi: 10.1107/S2053229614024218
  11. Dolomanov O.V., Bourhis L.J., Gildea R.J, Howard J.A.K., Puschmann H. J. Appl. Cryst. 2009, 42, 339. doi: 10.1107/S0021889808042726

Supplementary files

Supplementary Files
Action
1. JATS XML
2. Fig. General view of the molecule of compound 2b according to X-ray diffraction data. The dotted line shows the atoms and bonds of the minor conformer.

Download (250KB)
3. Scheme

Download (130KB)

Copyright (c) 2024 Russian Academy of Sciences