Complexes of nickel(II) carboxylates with pyridine and cyclam: crystal structures, mesomorphisms, and thermoelectrical properties

Synthesis of 4-alkoxypyridines as intermediates for zwitterionic liquid crystals

“…The method is relatively inexpensive and simple, but the ratio of the two isomers of the N-vs O-alkylated product depends on the reaction conditions. Thus, when the reaction is conducted with K2CO3 in DMF at ambient temperature, 1 [10] is obtained in 70% yield, 1 1 [16] in 89% yield, 3 and also 1 [12] was obtained under these conditions. 21 On the other hand, in MeCN solutions at reflux, the yield of 1 [12] was only 9%.…”

“…In most cases, 4-alkoxypyridines (1[n]) are N-substituted by reactions with metal-centered Lewis acids, 2,3,[20][21][22] organic electrophiles, 12,13,18,19,23,25 or boron electrophiles. 6,7,11 In rare cases C-positions of the pyridine ring in 1[n] are substituted before further transformations.…”

“…6,7,11 In rare cases C-positions of the pyridine ring in 1[n] are substituted before further transformations. 16,24 In spite of the increasing use of 4-alkoxypyridines (1[n]; n ≥ 3), only a handful are well characterized (1 [3], 29,30 5 ), some have partial data (1[4], 19,24,28 1[5], 7,28 1[8] 23 , 1[16] 4 ), while others are only mentioned in the literature without any data (1[6]), 20,27 1[14], 12 1[18] 12,22 ) and several homologs are not reported (e.g. 1 [11], 1 [13] and 1 [15]).…”

“…There is a rapidly growing interest in 4-alkoxypyridines 1[n] (n ≥ 3) as intermediates for soft materials such as liquid crystals [1][2][3][4][5] (including polar, [6][7][8][9][10][11] ionic [12][13][14][15] and quadrupolar species, such as 2[n] 10 in Figure 1), molecular electronics, 16 bio-active derivatives, [17][18][19] and also for research on organometallic complexes, [2][3][4][20][21][22] weak intermolecular interactions, 1,5 and various other aspects of organic chemistry. [23][24][25] Some 4-alkoxypyridines 1[n] have been shown to exhibit biological activity, such as inhibition of cytochrome P-450-catalyzed aniline hydroxylation 26,27 or gastric antisecretory activity.…”

Preparation of substituted alkoxypyridines via directed metalation and metal-halogen exchange

“…Various alkoxypyridines are found in pharmaceutical agents, [1][2][3] electronic materials, 4 liquid crystals, 5 organometallic complexes, [6][7][8] and oligomers. 9 They also have been used as synthetic building blocks for natural products and medicinal agents.…”