4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of 6-Alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles and 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles
Selected bond lengths (Å) | Selected bond angles (°) | |||||
---|---|---|---|---|---|---|
3b | ||||||
N(1)-C(13) | 1.346(2) | C(15)-C(11)-C(12) | 116.21(15) | |||
N(1)-C(14) | 1.318(2) | N(1)-C(13)-C(12) | 122.50(16) | |||
N(4)-C(13) | 1.337(2) | N(1)-C(14)-O(1) | 120.55(15) | |||
N(3)-C(16) | 1.1150(2) | N(1)-C(14)-C(15) | 124.42(16) | |||
C(12)-C(13) | 1.422(2) | C(11)-C(15)-C(14) | 119.28(16) | |||
C(11)-C(12) | 1.406(2) | C(13)-N(1)-C(14) | 117.46(15) | |||
O(1)-C(14) | 1.338(2) | N(4)-C(13)-N(1) | 116.87(16) | |||
C(11)-C(15) | 1.404(2) | C(14)-O(1)-C(18) | 119.91(14) | |||
C(15)-C(14) | 1.417(2) | C(17)-C(12)-C(13) | 116.37(15) | |||
O(1)-C(18) | 1.466(2) | C(12)-C(11)-C(6) | 120.99(15) | |||
4a | ||||||
N(1)-C(23) | 1.319(3) | N(1)-C(23)-C(22) | 120.62(18) | |||
C(24)-N(1) | 1.381(3) | N(1)-C(24)-C(25) | 124.48(19) | |||
C(22)-C(23) | 1.530(3) | N(1)-C(24)-O(1) | 116.55(18) | |||
C(21)-C(22) | 1.568(3) | C(23)-C(22)-C(21) | 106.96(16) | |||
C(21)-C(25) | 1.512(3) | C(22)-C(21)-C(25) | 106.41(16) | |||
C(25)-C(24) | 1.352(3) | C(21)-C(25)-C(24) | 118.82(18) | |||
C(22)-C(27) | 1.566(3) | N(1)-C(23)-N(2) | 120.29(19) | |||
C(23)-N(2) | 1.312(3) | N(2)-C(23)-C(22) | 118.99(18) | |||
C(24)-O(1) | 1.345(2) | C(27)-C (22)-C(26) | 107.67(17) | |||
4b | ||||||
N(1)-C(25) | 1.378(4) | C(24)-C(23)-C(22) | 105.9(3) | |||
N(1)-C(26) | 1.291(4) | N(4)-C(28)-C(24) | 177.4(4) | |||
N(2)-C(26) | 1.334(5) | N(2)-C(26)-C(22) | 118.3(3) | |||
N(3)-C(27) | 1.137(5) | N(3)-C(27)-C(22) | 178.0(4) | |||
N(4)-C(28) | 1.147(4) | C(26)-C(22)-C(23) | 103.3(3) | |||
C(22)-C(21) | 1.559(5) | C(24)-C(25)-N(1) | 124.1(3) | |||
C(22)-C(26) | 1.532(5) | N(2)-C(26)-N(1) | 119.3(3) | |||
C(23)-C(22) | 1.569(4) | C(21)-C(22)-C(23) | 111.6(3) | |||
C(24)-C(25) | 1.359(5) | C(26)-N(1)-C(25) | 117.0(3) | |||
C(23)-H(23) | 0.9800 | C(22)-C(26)-N(1) | 122.4(3) | |||
C(25)-O(1) | 1.345(4) | O(1)-C(25)-N(1) | 116.8(3) | |||
C(29)-O(1) | 1.443(5) | C(27)-C(22)-C(23) | 109.9(3) | |||
C(24)-C(23) | 1.510(5) | C(26)-C(22)-C(23) | 106.3(3) |
2.2. Electrochemistry
3. Experimental
3.1. General
3.2. Crystal Structures of 3b, 4a and 4b
4. Conclusions
Acknowledgments
Conflict of Interest
References
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Klimova, E.I.; Flores-Alamo, M.; Maya, S.C.; Martínez, M.E.; Ortiz-Frade, L.; Klimova, T. 4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry. Molecules 2012, 17, 10079-10093. https://doi.org/10.3390/molecules170910079
Klimova EI, Flores-Alamo M, Maya SC, Martínez ME, Ortiz-Frade L, Klimova T. 4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry. Molecules. 2012; 17(9):10079-10093. https://doi.org/10.3390/molecules170910079
Chicago/Turabian StyleKlimova, Elena I., Marcos Flores-Alamo, Sandra Cortez Maya, Mark E. Martínez, Luis Ortiz-Frade, and Tatiana Klimova. 2012. "4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry" Molecules 17, no. 9: 10079-10093. https://doi.org/10.3390/molecules170910079