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Mkrtchyan et al.
stirred with a water—hexane mixture (1 : 1, 50 mL) for 20 min.
The aqueous layer was separated and washed with hexane
(3×10 mL). The organic extracts were combined, dried with
Na2SO4, and distilled to give compounds 2a—e. The yields and
characteristics of compounds 2a—e are given in Tables 1 and 2.
Synthesis of βꢀamino enones 3a—d (general procedure). A soꢀ
lution of the corresponding βꢀalkoxy enone (1 mmol) in CHCl3
(2 mL) was added to a solution of PDA (1 mmol) in CHCl3
(5 mL). The reaction mixture was kept for 5 to 10 min and
passed through a column with silica gel (70—230, 3 cm). The
silica gel was washed with CHCl3 (6×10 mL) and the eluate was
concentrated. The yields and characteristics of compounds 3a—d
are given in Tables 2—5.
Synthesis of bis(βꢀamino enones) 4a—e (general procedure).
The corresponding βꢀalkoxy enone (1 mmol) was added to a
solution of PDA (0.5 mmol) in pyridine (3 mL). The reaction
mixture was stirred for 1—2 days and concentrated in vacuo. The
residue was dissolved in CHCl3 (10 mL), stirred with oxalic acid
(0.5 mmol) for 20 min, and filtered through a layer of silica
gel (70—230, 1 cm). The silica gel was washed with CHCl3
(4×10 mL) and the eluate was concentrated. The yields and
characteristics of compounds 4a—e are given in Tables 2—5.
Synthesis of bis(βꢀamino enones) 5a—c (general procedure).
The corresponding βꢀalkoxy enone 2 (0.1 mmol) was added to a
solution of βꢀamino enone (0.1 mmol) in pyridine (2 mL). The
reaction mixture was stirred for 1—2 days and then treated as
described above. The yields and characteristics of compounds
5a—c are given in Tables 2—5.
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The elemental analyses and registration of the IR and
NMR spectra were performed at the Center for Collective
Use of the Institute of Organic Synthesis, Ural Branch of
the Russian Academy of Sciences (Russian Foundation
for Basic Research, Project No. 00ꢀ03ꢀ40139).
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This work was financially supported by the Russian
Foundation for Basic Research (Project No. 02ꢀ03ꢀ32627)
and the Council on Grants of the President of the Rusꢀ
sian Federation (Program for State Support of Leading
Scientific Schools of the Russian Federation, Grant
NSh 1766.2003.3).
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Received May 30, 2005;
in revised form September 8, 2005