Purines, pyrimidines, and related fused systems. 20. Heterocyclizations of 6-alkynyl-1,3-dimethyllumazines. Synthesis of pyrrole and thiophene analogs of some natural pteridines
Publication type: Journal Article
Publication date: 2003-09-16
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
Sonogashira cross-coupling of 6-chloro-1,3-dimethyllumazine with terminal alkynes gave 6-alkynyl derivatives in good yields. Oxidative amination of the latter with primary alkylamines was accompanied by the pyrrole-ring closure to form 1-R"-2-R-6,8-dimethylpyrrolo[3,2-g]pteridine-5,7(6H,8H)-diones. The addition of bromine to 6-alkynyllumazines afforded the corresponding dibromoalkenes whose treatment with sodium trithiocarbonate gave rise to 2-R-6,8-dimethylthieno[3,2-g]pteridine-5,7(6H,8H)-diones. The latter compounds are close analogs of the metabolite of molybdenum cofactor (molybdopterine).
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Gulevskaya A. V., Shee D. V., Pozharskii A. F. Purines, pyrimidines, and related fused systems. 20. Heterocyclizations of 6-alkynyl-1,3-dimethyllumazines. Synthesis of pyrrole and thiophene analogs of some natural pteridines // Russian Chemical Bulletin. 2003. Vol. 52. No. 6. pp. 1403-1410.
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Gulevskaya A. V., Shee D. V., Pozharskii A. F. Purines, pyrimidines, and related fused systems. 20. Heterocyclizations of 6-alkynyl-1,3-dimethyllumazines. Synthesis of pyrrole and thiophene analogs of some natural pteridines // Russian Chemical Bulletin. 2003. Vol. 52. No. 6. pp. 1403-1410.
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TY - JOUR
DO - 10.1023/a:1024891530684
UR - https://doi.org/10.1023/a:1024891530684
TI - Purines, pyrimidines, and related fused systems. 20. Heterocyclizations of 6-alkynyl-1,3-dimethyllumazines. Synthesis of pyrrole and thiophene analogs of some natural pteridines
T2 - Russian Chemical Bulletin
AU - Gulevskaya, A V
AU - Shee, Dang Van
AU - Pozharskii, A F
PY - 2003
DA - 2003/09/16
PB - Springer Nature
SP - 1403-1410
IS - 6
VL - 52
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2003_Gulevskaya,
author = {A V Gulevskaya and Dang Van Shee and A F Pozharskii},
title = {Purines, pyrimidines, and related fused systems. 20. Heterocyclizations of 6-alkynyl-1,3-dimethyllumazines. Synthesis of pyrrole and thiophene analogs of some natural pteridines},
journal = {Russian Chemical Bulletin},
year = {2003},
volume = {52},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1023/a:1024891530684},
number = {6},
pages = {1403--1410},
doi = {10.1023/a:1024891530684}
}
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Gulevskaya, A. V., et al. “Purines, pyrimidines, and related fused systems. 20. Heterocyclizations of 6-alkynyl-1,3-dimethyllumazines. Synthesis of pyrrole and thiophene analogs of some natural pteridines.” Russian Chemical Bulletin, vol. 52, no. 6, Sep. 2003, pp. 1403-1410. https://doi.org/10.1023/a:1024891530684.