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Synlett

Volumn , Issue 3, 2007, Pages 431-434

A convenient one-pot aza-annulation of primary amines, acryloyl chloride and electron-deficient allenes

(3) Gray, Philip J a Motherwell, William B a Whitehead, Andrew J b

a UNIVERSITY COLLEGE LONDON (United Kingdom)

b GLAXOSMITHKLINE (United Kingdom)

Author keywords

Allenes; Enaminones; Heterocycles; Michael additions; Regioselectivity

Indexed keywords

ALKALOID DERIVATIVE; ALLENE DERIVATIVE; AMINE; CYCLOPENTAMINE;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; SYNTHESIS;

EID: 33847347254 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967955 Document Type: Article

Times cited : (6)

References (30)

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27
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28
- 33847345953
- General Procedure for the Synthesis of Enamides 10a, e and Spectroscopic Data for 10c. Amine 9c (1.0 mmol) was added to a solution of the allenic ketone (1.0 mmol) in anhyd MeCN (10 mL) at r.t. and then heated to reflux for 40 min under an atmosphere of nitrogen. The reaction mixture was cooled to r.t. and acryloyl chloride (1.1 mmol) was added. The reaction mixture was heated to reflux for a subsequent 1.5 h, cooled and concentrated under reduced pressure. The crude compound was purified by flash column chromatography (4:1 PE-EtOAc) to give the product (10c) as a clear oil. 1H NMR (300 MHz, CDCl3, δ, 1.65 (m, 1 H, CH, 2.01 (s, 3 H, Me, 2.14 (m, 1 H, CH, 2.44 (m, 1 H, CH, 2.56 (m, 1 H, CH, 2.90 (d, 1 H, J, 13.8 Hz, CH2Ph, 3.23 (d, 1 H, J, 13.8 Hz, CH2Ph, 3.77 (s, 3 H, OMe, 3.81 (s, 3 H, OMe, 4.62 (d, 1 H, J, 2.4 Hz, CH, 4.82 (d, 1 H, J, 2.4 Hz, CH, 4.96 s, 2 H, CH
- -1.

29
- 33847402627
- Procedure for the Synthesis of 13. Procedure identical to that for ref. 10c, however, 40 mg of p-TsOH was added after the addition of acryloyl chloride. The pyrrole was obtained as a white solid, mp 72-74°C. 1H NMR (300 MHz, CDCl3, δ, 1.79 (m, 1 H, CH, 2.19 (s, 3 H, Me, 2.36 (m, 1 H, CH, 2.57-2.69 (m, 2 H, CH2CO, 3.14 (d, 1 H, J, 13.8 Hz, CH2Ph, 3.41 (d, 1 H, J, 13.8 Hz, CH2Ph, 6.34 (t, 1 H, J, 3.3 Hz, ArH, 6.39 (m, 1 H, ArH, 7.05 (m, 2 H, ArH, 7.23-7.28 (m, 3 H, ArH, 7.41 (m, 1 H, ArH, 13C NMR (75 MHz, CDCl3, δ, 207.3, 167.7, 135.3, 134.0, 130.0, 128.4, 127.2, 117.6, 112.8, 111.9, 52.9, 43.3, 30.4, 28.2, 26.7. HRMS-FAB: m/z calcd for C17H17NO2: 268.13375; found [MH, 268.13321. IR (nujol, νmax, 2923, 2852, CH, 1705 C=O, 1456, 1400 cm-1
- -1.

30
- 33847396457
- General Procedure for the Synthesis of Azabicyclo [4.3.0] Systems 15a-c and 17. A solution of the allene (1.1 mmol, amine (1.1 mmol) and p-TsOH (40 mg) was heated to reflux for 40 min, cooled to r.t. and treated with acryloyl chloride (1.1 equiv, The reaction mixture was heated for a subsequent 8 h, cooled and concentrated at reduced pressure. Purification by chromatography (PE-EtOAc, 3:1) gave 15c as a pale yellow solid, mp 55-57°C. 1H NMR (300 MHz CDCl3, δ, 1.70 (t, 3 H, J, 7.1 Hz, CH3, 2.25 (m, 1 H, CH2CO) 2.40 (m, 1 H, CH2CHCO2Et, 2.70 (m, 1 H, CH2CHCO 2Et, 2.99 (m, 1 H, CH2CO, 3.80 (s, 2 H, CH 2Ph, 3.94 (m, 1 H, CHCO2Et) 4.03 (m, 2 H, CH 2CH3) 6.10 (d, 1 H, J, 3.4 Hz, ArH, 7.14-7.37 (m, 5 H, ArH, 7.37 (d, 1 H, J, 3.4 Hz, ArH, 13C NMR 75 MHz, CDCl3
- -1.

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