- Synthesis and structural studies of new asymmetric pyridyl-tetrazole ligands for supramolecular chemistry
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The synthesis of asymmetric diester derivatives of pyridyl-tetrazole ligands was successfully undertaken. Five crystal structures are reported including three asymmetric diesters (one of which is a mixed methyl ethyl ester derivative), a dicarboxylic acid and a monosodium (dicarboxylic acid)(monoacid-carboxylate) dihydrate intermediate. The dicarboxylic acid assembles by an unusual and unexpected route with the primary assembly based on carboxylic…pyridine (COOH?N) synthons that form an unusual cyclic hydrogen bonded ring with the R22(17) motif. Assembly in hydrogen bonding motifs using ‘odd’ numbers of atoms is the exception rather than the rule.
- Sheridan, Ursula,Gallagher, John F.,McGinley, John
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- A Bifunctional Reagent Designed for the Mild, Nucleophilic Functionalization of Pyridines
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Herein is reported the design and application of a reagent for the direct functionalization of pyridines. These reactions occur under mild conditions and exhibit broad functional group tolerance, enabling the late-stage functionalization of drug-like molecules. The reagent can be easily prepared on large scale from inexpensive reagents, and reacts in the title reaction with acetonitrile, sodium chloride, and sodium methanesulfonate as the sole byproducts. Although this Communication focuses primarily on reactions with cyanide as nucleophile, preliminary experiments with other nucleophiles foreshadow the broad reaching synthetic utility of this approach.
- Fier, Patrick S.
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supporting information
p. 9499 - 9502
(2017/07/24)
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- HOMOLYTIC ALKOXYCARBONYLATION REACTIONS IN TWO-PHASE SYSTEMS 3. INTRODUCTION OF A SINGLE CARBOXYLIC ACID ESTER FUNCTION INTO CYANO- OR ALKOXYCARBONYL SUBSTITUTED N-HETEROAROMATICS
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Homolytic alkoxycarbonylation reactions with cyanopyridines 1a, 2a, 3a, alkyl pyridinecarboxylates 1b, 2b, 3b, 3c and ethyl 4-pyridazinecarboxylate 4 in presence of dichloromethane were studied.It is demonstrated that under these conditions multiple substitution in general is suppressed markedly.Thus, this experimentally simple procedure represents an efficient and versatile method for single-step preparations of alkyl cyanopyridinecarboxylates 7a, 8a, 9a, 10a.Furthermore, it provides convenient access to so far not available mixed esters 5b, 7b, 8b, 10b, 13, derived from 2,3-pyridine-, 2,4-pyridine-, 3,4-pyridine and 4,5-pyridazinedicarboxylic acid.
- Heinisch, Gottfried,Loetsch, Gerhard
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p. 731 - 744
(2007/10/02)
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- Site-Selectivity in the Cyanation of 3-Substituted Pyridine 1-Oxides with Trimethylsilanecarbonitrile
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The cyanation of 3-halo-, 3-methoxy-, and 3-dimethylaminopyridine 1-oxide with trimethylsilanecarbonitrile gave predominantly the corresponding 3-substituted 2-pyridinecarbonitriles.The deoxygenation of nitropyridine 1-oxides to nitropyridines with the same reagent is also described.Keywords - site-selective reaction; trimethylsilanecarbonitrile; pyridine 1-oxide; 2-pyridine-carbonitrile; nitropyridine 1-oxide; deoxygenation; aromatic amine N-oxide; cyanation
- Sakamoto, Takao,Kaneda, Soh-ichi,Nishimura, Sumiko,Yamanaka, Hiroshi
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p. 565 - 571
(2007/10/02)
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