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DOI: 10.1055/s-0030-1258519
Intramolecular Aza-Wittig Reaction: A New Efficient Tool for the Construction of Piperazine 2,5-Dione Derivatives
Publikationsverlauf
Publikationsdatum:
27. Juli 2010 (online)

Abstract
A new efficient approach for the synthesis of unsymmetricaly substituted piperazine 2,5-dione derivatives is described by using intramolecular aza-Wittig reaction as the key step. The reaction conditions are very simple, offer easy isolation, and excellent yields of the products.
Key words
piperazine 2,5-dione - intramolecular aza-Wittig reaction - iminophosphorane - cyclization
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- Supporting Information
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References and Notes
General Procedure
for the Preparation of Compound 6a
To a solution of
compound 3a (100 mg, 0.36 mmol) in THF (5
mL) was added Ph3P (142 mg, 0.54 mmol). The mixture was
stirred at r.t. for 30 min. After completion of the reaction (as
monitored by TLC), THF was completely evaporated, and the crude
product was purified by column chromatog-raphy over silica gel (60-120
mesh) using PE-EtOAc (1:1) as eluant to give the pure product 6a in 96% yield.
Yield
96%, solid, mp 208-210 ˚C. IR
(KBr): νmax = 1655, 1689,
3243 cm-¹. ¹H NMR
(400 MHz, CDCl3): δ = 7.27-7.38
(m, 5 H), 6.26 (br s, 1 H), 4.61 (s, 2 H), 4.10 (s, 2 H), 3.86 (s,
2 H). ¹³C NMR (125 MHz, DMSO-d
6): δ = 44.4, 48.2,
49.0, 127.4, 127.8, 128.5, 136.2, 164.3, 165.5. HRMS: m/z calcd for C11H12N2O2:
227.0797 [M+ + Na];
found: 227.0797 [M+ + Na].