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

A. I. Kobelev; Кобелев Александр Иванович; M. V. Dmitriev; Дмитриев Максим Викторович; A. N. Maslivets; Масливец Андрей Николаевич

doi:10.31857/S0514749224040109

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

Authors: Kobelev A.I.¹, Dmitriev M.V.¹, Maslivets A.N.¹
Affiliations:
1. Perm State University
Issue: Vol 60, No 4 (2024)
Pages: 495-501
Section: Articles
URL: https://rjmseer.com/0514-7492/article/view/672172
DOI: https://doi.org/10.31857/S0514749224040109
EDN: https://elibrary.ru/RYUBSQ
ID: 672172

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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.

Keywords

hetareno[e]pyrrole-2,3-diones, 3-aroylpyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones, pyrrolobenzoxazinetriones, 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, spiro[pyrrole-2,3′-pyrroles], spiro[pyrrole-2,5′-pyrrolo[2,3-d]pyrimidine], X-ray diffraction analysis

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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

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3. Fig. General view of the molecule of 3-benzoyl-4-hydroxy-1-(2-hydroxyphenyl)-1′,3′-dimethylspiro[pyrrole-2,5′-pyrrolo[2,3-d]pyrimidine]-2′,4′,5,6′ (1H,1′H,3′H,7′H)-tetraone (2a) according to X-ray diffraction data in thermal ellipsoids of 30% probability