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Straightforward synthesis of functionalized furo[3,4-d] pyrimidine-2,4-diones

Laurens De Coen (UGent) , Martyna Jatczak (UGent) , Koen Muylaert (UGent) , Sven Mangelinckx (UGent) and Christian Stevens (UGent)
(2015) SYNTHESIS-STUTTGART. 47(9). p.1227-1237
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Abstract
An efficient synthesis of furo[3,4-d]pyrimidine-2,4-diones has been accomplished via a straightforward three-step pathway. Curtius rearrangement of 4-(methoxycarbonyl)furan-3-carboxylic acid and subsequent reaction with a variety of amines resulted in the corresponding intermediate ureids, which could be ring closed to the bicyclic scaffold in good yields. Functionalization of N-1 afforded a small library of new heterocycles. (Partial) hydrogenation of the furo[3,4-d]pyrimidine- 2,4-diones led to the 5,7-dihydro- and tetrahydrofuro[3,4-d]pyrimidine- 2,4-diones.
Keywords
ring closure, alkylation, heterocycles, rearrangement, hydrogenation, CANCER-THERAPY, MTOR INHIBITORS

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MLA
De Coen, Laurens et al. “Straightforward Synthesis of Functionalized Furo[3,4-d] Pyrimidine-2,4-diones.” SYNTHESIS-STUTTGART 47.9 (2015): 1227–1237. Print.
APA
De Coen, L., Jatczak, M., Muylaert, K., Mangelinckx, S., & Stevens, C. (2015). Straightforward synthesis of functionalized furo[3,4-d] pyrimidine-2,4-diones. SYNTHESIS-STUTTGART, 47(9), 1227–1237.
Chicago author-date
De Coen, Laurens, Martyna Jatczak, Koen Muylaert, Sven Mangelinckx, and Christian Stevens. 2015. “Straightforward Synthesis of Functionalized Furo[3,4-d] Pyrimidine-2,4-diones.” Synthesis-stuttgart 47 (9): 1227–1237.
Chicago author-date (all authors)
De Coen, Laurens, Martyna Jatczak, Koen Muylaert, Sven Mangelinckx, and Christian Stevens. 2015. “Straightforward Synthesis of Functionalized Furo[3,4-d] Pyrimidine-2,4-diones.” Synthesis-stuttgart 47 (9): 1227–1237.
Vancouver
1.
De Coen L, Jatczak M, Muylaert K, Mangelinckx S, Stevens C. Straightforward synthesis of functionalized furo[3,4-d] pyrimidine-2,4-diones. SYNTHESIS-STUTTGART. 2015;47(9):1227–37.
IEEE
[1]
L. De Coen, M. Jatczak, K. Muylaert, S. Mangelinckx, and C. Stevens, “Straightforward synthesis of functionalized furo[3,4-d] pyrimidine-2,4-diones,” SYNTHESIS-STUTTGART, vol. 47, no. 9, pp. 1227–1237, 2015.
@article{5956099,
  abstract     = {An efficient synthesis of furo[3,4-d]pyrimidine-2,4-diones has been accomplished via a straightforward three-step pathway. Curtius rearrangement of 4-(methoxycarbonyl)furan-3-carboxylic acid and subsequent reaction with a variety of amines resulted in the corresponding intermediate ureids, which could be ring closed to the bicyclic scaffold in good yields. Functionalization of N-1 afforded a small library of new heterocycles. (Partial) hydrogenation of the furo[3,4-d]pyrimidine- 2,4-diones led to the 5,7-dihydro- and tetrahydrofuro[3,4-d]pyrimidine- 2,4-diones.},
  author       = {De Coen, Laurens and Jatczak, Martyna and Muylaert, Koen and Mangelinckx, Sven and Stevens, Christian},
  issn         = {0039-7881},
  journal      = {SYNTHESIS-STUTTGART},
  keywords     = {ring closure,alkylation,heterocycles,rearrangement,hydrogenation,CANCER-THERAPY,MTOR INHIBITORS},
  language     = {eng},
  number       = {9},
  pages        = {1227--1237},
  title        = {Straightforward synthesis of functionalized furo[3,4-d] pyrimidine-2,4-diones},
  url          = {http://dx.doi.org/10.1055/s-0034-1380321},
  volume       = {47},
  year         = {2015},
}

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