Synlett 2013; 24(15): 1949-1952
DOI: 10.1055/s-0033-1339486
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Three-Component Barbier-Type Reaction for the Synthesis of β-Nitroamines

Raquel G. Soengas*
Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Fax: +351(234)370084   Email: [email protected]   Email: [email protected]
,
Artur M. S. Silva*
Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Fax: +351(234)370084   Email: [email protected]   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 24 June 2013

Accepted: 30 June 2013

Publication Date:
07 August 2013 (online)


Abstract

The combination of an aldehyde, bromonitromethane, and p-methoxyaniline in the presence of tin(II) chloride and titanium tetraethoxide allows a straightforward access to β-nitroamine derivatives. The use of solid paraformaldehyde results in the amino methylation of methylnitronate. On the other hand, chiral sugar-derived aldehydes furnished the corresponding nitrosugars in high yields and stereoselectivities.

Supporting Information

 
  • References and Notes

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  • 21 Analytical Data of 3-O-Benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-p-methoxyphenylamino-6-nitro-α-d-glucofuranose (4k): yellow oil; Rf 0.28 (hexane–EtOAc, 3:1); [α]D 27 –9.2º (c = 0.6 in CHCl3). 1H NMR (500 MHz, CDCl3): δ = 7.12–7.34 (m, 5 H), 6.54 (d, J = 9.0 Hz, 2 H), 6.34 (d, J = 9.0 Hz, 2 H), 5.83 (d, J = 3.6 Hz, 1 H), 4.67 (dd, J = 13.1, 3.9 Hz, 1 H), 4.44–4.59 (m, 3 H), 4.38–4.42 (m, 1 H), 4.17–4.24 (m, 3 H), 4.02 (d, J = 3.1 Hz, 1 H), 3.73 (s, 3 H), 1.47 (s, 3 H), 1.31 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 153.3 (C), 139.3 (C), 136.9 (C), 128.4 (2 × CH), 128.0 (CH), 127.9 (2 × CH), 116.3 (2 × CH), 114.9 (2 × CH), 112.1 (C), 104.9 (CH), 81.9 (CH), 81.2 (CH), 79.9 (CH), 75.8 (CH2), 72.1 (CH2), 55.6 (Me), 51.9 (CH), 26.7 (Me), 26.2 (Me). MS (ESI+): m/z (%) = 445 (100) [M + H]+, 444 (1), 316 (5), 289 (1), 288 (21). HRMS (ESI+): m/z [M + H]+ calcd for [C23H29N2O7]+: 445.1975; found: 445.1969. IR (neat): 3380, 1556, 1513, 1377, 1241 cm–1.
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