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Synlett 2017; 28(02): 207-213
DOI: 10.1055/s-0036-1588882
letter
© Georg Thieme Verlag Stuttgart · New York

Use of α,ω-Dichloroketimine Building Blocks for the Construction of 1-Azabicyclo[3.1.0]hexanes, Piperidines, Pyridines, Pyrroles, and Tetrahydroindoles

Nicola Piens
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium   Email: matthias.dhooghe@UGent.be   Email: norbert.dekimpe@UGent.be
,
Wim Aelterman
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium   Email: matthias.dhooghe@UGent.be   Email: norbert.dekimpe@UGent.be
,
Matthias D’hooghe*
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium   Email: matthias.dhooghe@UGent.be   Email: norbert.dekimpe@UGent.be
,
Norbert De Kimpe*
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium   Email: matthias.dhooghe@UGent.be   Email: norbert.dekimpe@UGent.be
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Further Information

Publication History

Received: 19 August 2016

Accepted after revision: 24 August 2016

Publication Date:
13 September 2016 (online)

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Abstract

A variety of different N-[2-chloro-4-(chloromethyl)pent-4-enylidene]amines and N-(2,6-dichlorohex-4-enylidene)amines was prepared for the first time, and their reactivity as eligible building blocks for the synthesis of biologically relevant nitrogen-containing heterocyclic compounds was studied. In this way, a convenient entry into functionalized 1-azabicyclo[3.1.0]hexanes, piperidines, pyridines, pyrroles, and tetrahydroindoles was developed, pointing to the broad synthetic flexibility of these dichlorinated imine substrates.

Key words

α,ω-dichloroketimines - 1-azabicyclo[3.1.0]hexanes - piperidines - pyridines - pyrroles - tetrahydroindoles

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588882.
  • Supporting Information
 

  • References and Notes

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  • 24 cis-1-Chloro-3-isopropyl-2-phenyl-4,5,5a,11a-tetrahydro-3H-naphtho[2,3-e]indole-6,11-dione (22a) Light-brown solid; yield 72% (2 mmol); mp 197.7–198.4 °C; Rf = 0.24 (hexane–EtOAc = 85:15). 1H NMR (270 MHz, CDCl3): δ = 1.34 (3 H, d, J = 6.9 Hz), 1.37 (3 H, d, J = 6.9 Hz), 1.93–2.37 (2 H, m), 2.71–3.04 (2 H, m), 3.33 (1 H, ddd, J = 11.7, 5.6, 2.8 Hz), 4.32 (1 H, d, J = 5.6 Hz), 4.36 (1 H, sept, J = 6.9 Hz), 7.31–7.48 and 7.71–7.80 and 8.04–8.17 (9 H, m). 13C NMR (68 MHz, CDCl3): δ = 22.4, 22.6, 23.8, 26.6, 46.5, 48.9, 49.0, 109.8, 112.4, 126.4, 127.0, 127.2, 127.9, 128.3, 129.7, 131.1, 131.4, 133.6, 134.1, 134.6, 135.7, 196.0, 198.8. IR (KBr): νmax = 1667, 1587, 1351, 1286, 1249, 1213 cm–1. MS (70 eV): m/z (%) = 403/5 (100) [M+], 389/91 (7), 388/90 (20), 368 (29), 360 (6), 346 (11), 326 (13), 324 (12), 317 (6), 298 (7), 280 (9), 270 (8), 245 (5), 228 (15), 203 (11), 194 (11), 193 (34), 165 (13), 152 (6), 133 (36), 125 (6), 105 (27), 104 (23), 89 (8), 77 (20), 76 (18), 57 (15), 43 (32).