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Search for "2-alkylpyridines" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.

Direct C(sp3)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

  • Siyu Wang,
  • Lianyou Zheng,
  • Shutao Wang,
  • Shulin Ning,
  • Zhuoqi Zhang and
  • Jinbao Xiang

Beilstein J. Org. Chem. 2021, 17, 2505–2510, doi:10.3762/bjoc.17.167

Graphical Abstract
  • (sp3)–H allylic alkylation of 2-alkylpyridines with Morita–Baylis–Hillman (MBH) carbonates is described. A plausible mechanism of the reaction might involve a tandem SN2’ type nucleophilic substitution followed by an aza-Cope rearrangement. Various alkyl substituents on 2-alkylpyridines were tolerated
  • in the reaction to give the allylation products in 26–91% yields. The developed method provides a straightforward and operational simple strategy for the allylic functionalization of 2-alkypyridine derivatives. Keywords: 2-alkylpyridines; allylic alkylation; aza-Cope rearrangement; catalyst-free
  • reported C(sp3)–H allylic substitution reactions were mainly applied on the 2-alkyl-azaarenes containing strong electron-withdrawing groups. While the reactions with inactive alkyl-aza-arenes were rare [30][31]. Kim et al. have reported a K2CO3-promoted one-pot allylation reaction of 2-alkylpyridines with
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Letter
Published 01 Oct 2021

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

  • Igor B. Krylov,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

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  • . The benzylic position of 2-alkylpyridines and related compounds 82 was acetoxylated using the Pd(OAc)2/CuI catalytic system in acetic acid under an oxygen pressure of 8 atm to prepare products 83 (Scheme 18) [78]. The acyloxylation of methyl or methylene groups of 8-methylquinoline and its derivatives
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Review
Published 20 Jan 2015

Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5

  • Ulrike Groenhagen,
  • Michael Maczka,
  • Jeroen S. Dickschat and
  • Stefan Schulz

Beilstein J. Org. Chem. 2014, 10, 1421–1432, doi:10.3762/bjoc.10.146

Graphical Abstract
  • and related compounds. We investigated the strain for the production of volatiles using the CLSA (closed-loop stripping analysis) method. Liquid and agar plate cultures revealed the formation of new 2-alkylpyridines (streptopyridines), structurally closely related to the already known 2
  • that the side chain contained only one double bond, the position of which had to be determined. A 1-pentenyl side chain seemed unlikely because of the high abundance of the m/z 93 ion in the mass spectrum of 8, which we assumed is a McLafferty ion that is commonly observed in 2-alkylpyridines [16
  • cross-coupling and proved to be identical to the natural products. 2-Alkylpyridines have been reported earlier as aroma components, like 2-butylpyridine or 2-pentylpyridine (7) identified in fried chicken [18], or 2-propylpyridine (6), present in sesame seed oil [19], but are not known from bacteria
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Published 24 Jun 2014
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