Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship

Mohamed Yacine Ameur Messaoud, Ghenia Bentabed-Ababsa, Madani Hedidi, Aïcha Derdour, Floris Chevallier, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Laurent Picot, Valérie Thiéry, Thierry Roisnel, Vincent Dorcet and Florence Mongin

Beilstein J. Org. Chem. 2015, 11, 1475–1485. https://doi.org/10.3762/bjoc.11.160

Supporting Information

Supporting Information File 1: Experimental description of the synthesized compounds, 1H and 13C NMR spectra, calculated values of the Gibbs energies ΔGacid [kcal·mo1−1] for deprotonation, selected Cartesian coordinates of molecular geometry for the most stable rotamer forms optimized at B3LYP/6-31G(d) level of theory.
Format: PDF Size: 3.1 MB Download
Supporting Information File 2: CIF files of 2e (CCDC1402111), 4c (1402112), 3d (1402113), 3e (1402114), and 5d (1402115). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
Format: CIF Size: 619.2 KB Download
Back To Article

Latest Articles

Navigating and expanding the roadmap of natural product genome mining tools

  1. Friederike Biermann,
  2. Sebastian L. Wenski and
  3. Eric J. N. Helfrich
  • Perspective
  • Published 06 Dec 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1656–1671, doi:10.3762/bjoc.18.178

A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition

  1. Anastasia Vepreva,
  2. Alexander Yanovich,
  3. Dmitry Dar’in,
  4. Grigory Kantin,
  5. Alexander Bunev and
  6. Mikhail Krasavin
  • Full Research Paper
  • Published 06 Dec 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1649–1655, doi:10.3762/bjoc.18.177

Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone

  1. Motoyuki Isoda,
  2. Kazuyuki Sato,
  3. Kenta Kameda,
  4. Kana Wakabayashi,
  5. Ryota Sato,
  6. Hideki Minami,
  7. Yukiko Karuo,
  8. Atsushi Tarui,
  9. Kentaro Kawai and
  10. Masaaki Omote
  • Full Research Paper
  • Published 02 Dec 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1642–1648, doi:10.3762/bjoc.18.176

A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction

  1. Ksenia Malkova,
  2. Andrey Bubyrev,
  3. Vasilisa Krivovicheva,
  4. Dmitry Dar’in,
  5. Alexander Bunev and
  6. Mikhail Krasavin
  • Letter
  • Published 02 Dec 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175

  • Full Research Paper
  • Published 01 Dec 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1629–1635, doi:10.3762/bjoc.18.174

Synthetic study toward the diterpenoid aberrarone

  1. Liang Shi,
  2. Zhiyu Gao,
  3. Yiqing Li,
  4. Yuanhao Dai,
  5. Yu Liu,
  6. Lili Shi and
  7. Hong-Dong Hao
  • Letter
  • Published 30 Nov 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1625–1628, doi:10.3762/bjoc.18.173

A new route for the synthesis of 1-deazaguanine and 1-deazahypoxanthine

  1. Raphael Bereiter,
  2. Marco Oberlechner and
  3. Ronald Micura
  • Full Research Paper
  • Published 29 Nov 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1617–1624, doi:10.3762/bjoc.18.172

One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

  1. Juan Lu,
  2. Bin Yao,
  3. Desheng Zhan,
  4. Zhuo Sun,
  5. Yun Ji and
  6. Xiaofeng Zhang
  • Full Research Paper
  • Published 28 Nov 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1607–1616, doi:10.3762/bjoc.18.171

  • Full Research Paper
  • Published 25 Nov 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

Formal total synthesis of macarpine via a Au(I)-catalyzed 6-endo-dig cycloisomerization strategy

  1. Jiayue Fu,
  2. Bingbing Li,
  3. Zefang Zhou,
  4. Maosheng Cheng,
  5. Lu Yang and
  6. Yongxiang Liu
  • Letter
  • Published 23 Nov 2022
Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1589–1595, doi:10.3762/bjoc.18.169

Latest Thematic Issues

Other Beilstein-Institut Open Science Activities

Keep Informed

RSS Feed

Subscribe to our Latest Articles RSS Feed.

Subscribe

Follow the Beilstein-Institut

LinkedIn

Twitter: @BeilsteinInst