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Synlett 2017; 28(02): 207-213
DOI: 10.1055/s-0036-1588882
DOI: 10.1055/s-0036-1588882
letter
Use of α,ω-Dichloroketimine Building Blocks for the Construction of 1-Azabicyclo[3.1.0]hexanes, Piperidines, Pyridines, Pyrroles, and Tetrahydroindoles
Authors
Further Information
Publication History
Received: 19 August 2016
Accepted after revision: 24 August 2016
Publication Date:
13 September 2016 (online)
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 - tetrahydroindolesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588882.
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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).