Synthesis of 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5- oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones and reaction thereof with acetic anhydride

Tetrahedron Letters

Volumn 47, Issue 4, 2006, Pages 557-560

  Shchepin, Vasiliy V ^a   Silaychev, Pavel S ^a   Rakitin, Anton R ^b   Kodess, Mikhayl I ^c  

^a PERM STATE UNIVERSITY   (Russian Federation)

^b OOO PermNIPIneft   (Russian Federation)

^c INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

1,2,9b,9c Tetrahydro 5 oxo 2 aza cyclopenta 2,3 cyclopropa 1, 2 a naphthalene 3,4 diones; 1 Aryl 2,2 dibromoalkanones; 2 Oxochromen 3 carboxylic acid N benzylamide; Zinc; Zinc enolate

Indexed keywords

ACETIC ANHYDRIDE; CHROMENE DERIVATIVE; KETONE DERIVATIVE; NAPHTHALENE DERIVATIVE; ZINC;

ACYLATION; ARTICLE; CHEMICAL REACTION; ISOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 29144520487     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.036     Document Type: Article

References (11)

1. N. Kamubat, T. Fujii, M. Naka, and S. Yamashita Bull. Chem. Soc. Jpn. 50 1977 1005
2. L.T. Scott, and W.D. Cotton J. Am. Chem. Soc. 95 1973 5416
3. T. Matsuki, N.X. Hu, Y. Aso, T. Otsubo, and F. Ogura Bull. Chem. Soc. Jpn. 62 1989 2105
4. J.C. Le Menn, and A.T.J. Sarrazin Can. J. Chem. 69 1991 761
5. V.V. Shchepin, A.A. Tryastsin, R.V. Shchepin, M.M. Kalyuzhnyi, and S.B. Lewis Russ. J. Org. Chem. 37 2001 1669
6. V.V. Shchepin, M.M. Kalyuzhnyi, R.V. Shchepin, and M.I. Vakhrin Russ. J. Gen. Chem. 73 2003 802
7. V.V. Shchepin, M.M. Kalyuzhnyi, P.S. Silaychev, N.Yu. Russkikh, R.V. Shchepin, M.A. Ezhikova, and M.I. Kodess Russ. J. Org. Chem. 9 2004 1353
8. General procedure for synthesizing compounds 7: The 1-aryl-2,2- dibromoalkanone (0.03 mol) was added to fine zinc chips (4 g) and diethyl ether (8 ml) and ethyl acetate (10 ml). The mixture was initially heated to start a spontaneous reaction. After the reaction was complete, the mixture was boiled for 15 min, cooled, and was decanted off the zinc into a different flask. This was followed by the addition of compounds 3a,b (0.01 mol), boiling for 30-40 min, cooling, and hydrolyzing with acetic acid. The reaction products were extracted, the solvent was evaporated, and the residue was recrystallized from acetone or methanol. Ratios of not less than 2:1 between the 1-aryl-2,2-dibromoalkanone and compounds 3a,b were found to be necessary for the reaction to take place.
9. 4 (583.3): calcd, %: C 55.60, H 3.63; found, %: C 55.47, H 3.54.
10. General procedure for synthesizing compounds 9: 8-R-9c-alkyl-1-aryl-2- benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1, 2-a]naphthalene-3,4-dione (0.005 mol) was boiled with excess acetic anhydride and three drops of n-tributylamine for 3 h followed by evaporation of the acetic acid formed and unreacted acetic anhydride. The residue was dissolved in boiling benzene and salted out with petroleum ether. After precipitation the reaction product was recrystallized from ethyl acetate. Acetylation did not proceed and starting material was recovered when the reaction was carried out at room temperature.
11. 5 (532.4): calcd, %: C 63.17, H 4.17, N 2.63; found, %: C 63.01, H 4.08, N 2.49.