A general strategy for the synthesis of difluoromethyl-containing pyrazoles, pyridines and pyrimidines
Difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles are prepared by a two step method. The regioselective cyclizations of electron-excessive aminoheterocycles, hydrazines and amidines with CF 2Cl-substituted 1,3-dicarbonyl compounds provide the corresponding CF 2Cl-substit...
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| Published in | Tetrahedron Vol. 67; no. 31; pp. 5663 - 5677 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
05.08.2011
Elsevier |
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| Abstract | Difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles are prepared by a two step method. The regioselective cyclizations of electron-excessive aminoheterocycles, hydrazines and amidines with CF
2Cl-substituted 1,3-dicarbonyl compounds provide the corresponding CF
2Cl-substituted heterocycles. Subsequent radical reactions with trimethylstannane or allyltrimethylstannane gave difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles, respectively.
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| AbstractList | Difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles are prepared by a two step method. The regioselective cyclizations of electron-excessive aminoheterocycles, hydrazines and amidines with CF2Cl-substituted 1,3-dicarbonyl compounds provide the corresponding CF2Cl-substituted heterocycles. Subsequent radical reactions with trimethylstannane or allyltrimethylstannane gave difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles, respectively. (C) 2011 Elsevier Ltd. All rights reserved. Difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles are prepared by a two step method. The regioselective cyclizations of electron-excessive aminoheterocycles, hydrazines and amidines with CF sub(2Cl-substituted 1,3-dicarbonyl compounds provide the corresponding CF) sub(2)Cl-substituted heterocycles. Subsequent radical reactions with trimethylstannane or allyltrimethylstannane gave difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles, respectively. Difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles are prepared by a two step method. The regioselective cyclizations of electron-excessive aminoheterocycles, hydrazines and amidines with CF 2Cl-substituted 1,3-dicarbonyl compounds provide the corresponding CF 2Cl-substituted heterocycles. Subsequent radical reactions with trimethylstannane or allyltrimethylstannane gave difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles, respectively. [Display omitted] |
| Author | Specowius, Verena Iaroshenko, Viktor O. Vlach, Katharina Mkrtchyan, Satenik Vilches-Herrera, Marcelo Ostrovskyi, Dmytro Villinger, Alexander Langer, Peter |
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| Keywords | Organofluorine compounds N-Heterocycles Cyclizations Regioselectivity Purine isosteres POTENT EFFICACY VIVO PHARMACOKINETICS DRUGS INHIBITORS ANTAGONISTS Purine derivatives Nitrogen heterocycle Isostere Purine base Diketone Free radical reaction Pyridine derivatives Amidine Pyridine Cyclization Pyrazole derivatives Pyrimidine derivatives Fluorine Organic compounds Hydrazine Chemical synthesis |
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| Snippet | Difluoromethyl-containing heteroannulated pyridines, pyrimidines and pyrazoles are prepared by a two step method. The regioselective cyclizations of... |
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| SubjectTerms | Chemistry Chemistry, Organic Cyclizations Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Hydrazines N-Heterocycles Organic chemistry Organofluorine compounds Physical Sciences Preparations and properties Purine isosteres Pyrazole Pyridines Pyrimidines Radicals Regioselectivity Science & Technology Strategy Synthesis (chemistry) Tetrahedrons |
| Title | A general strategy for the synthesis of difluoromethyl-containing pyrazoles, pyridines and pyrimidines |
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