2010
DOI: 10.1002/poc.1781
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Synthesis and properties of di‐ and trinitrobenzyl substituted pyridine derivates

Abstract: A new method to obtain di‐ and trinitrobenzyl substituted pyridines is presented in this paper. By systematic variation of reaction parameters, the reaction conditions were optimized. The novel synthesis circumvents the commonly used nitration of benzyl pyridines, and thus avoids the nitration of the heterocycle which is a common side reaction. Furthermore, the starting materials for the synthesis of a variety of photochromic nitrobenzyl pyridines are easily accessible. The half‐lives of the phototautomers of … Show more

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Cited by 6 publications
(3 citation statements)
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“…Compared to the conventional F À triggered Si-O cleavage, the more larger red-shift (E287 nm) when TBAF was added to 4 may be attributed to the presence of an enhanced p-conjugation network involving the naphthalimide moiety and the 2-(cyanomethyl) pyridine. 8 After the addition of 5.40 equivalents of F À , an instantaneous colorimetric change from colourless to deep blue (Fig. 1, inset, naked-eye detection) was observed.…”
mentioning
confidence: 94%
“…Compared to the conventional F À triggered Si-O cleavage, the more larger red-shift (E287 nm) when TBAF was added to 4 may be attributed to the presence of an enhanced p-conjugation network involving the naphthalimide moiety and the 2-(cyanomethyl) pyridine. 8 After the addition of 5.40 equivalents of F À , an instantaneous colorimetric change from colourless to deep blue (Fig. 1, inset, naked-eye detection) was observed.…”
mentioning
confidence: 94%
“…Reaction of 6s, a substrate lacking an electronegative atom or electron-withdrawing group at the benzylic position to facilitate anhydrobase formation, was sluggish and required prolonged heating with a large excess of ClCO 2 Et/Et 3 N to reach completion. It is notable that S N Ar reactions involving alkylpyridine nucleophiles are rare, 19 and the transformations shown in Scheme 2 proceed under relatively mild conditions. The 3,3-disubstituted oxindole ring system is a common heterocyclic scaffold found in numerous natural products and bioactive small molecules.…”
mentioning
confidence: 99%
“…A prototype is 2-nitrotoluene, which forms an aci-nitro derivative when irradiated, 4 and several derivatives thereof have been developed. 5 By placing such a photoacid on one side on the membrane, a pH gradient can be generated by irradiation.…”
mentioning
confidence: 99%