Subscribe to RSS
DOI: 10.1055/s-2003-37104
‘Michael-Michael-Wittig’ Reactions of (2,4-Dioxobutylidene)phosphoranes with 3-Formylchromones
Publication History
Publication Date:
07 February 2003 (online)
Abstract
4-(2′-Hydroxybenzoyl)salicylic esters and amides were prepared by domino ‘Michael-retro-Michael-Wittig’ reactions of (2,4-dioxobutylidene)triphenylphosphoranes with 3-formylchromones.
Key words
Michael-Michael-Wittig-reaction - 4-(2′-hydroxybenzoyl)salicylic esters - 4-(2′-hydroxybenzoyl)salicylic amides - (2,4-dioxobutylidene)triphenylphosphoranes
- 1
Römpp Lexikon Naturstoffe
Steglich W.Fugmann B.Lang-Fugmann S. Thieme; Stuttgart: 1997. -
2a
Ezaki N.Shomura T.Koyama M.Niwa T.Kojima M.Inouye S.Niida T. J. Antibiot. 1981, 34: 1363 -
2b
Kaneda M.Nakamura S.Ezaki N.Iitaka Y. J. Antibiot. 1981, 34: 1366 -
2c
Ezaki N.Koyama M.Shomura T.Tsuruoka T.Inouye S. J. Antibiot. 1983, 36: 1263 -
2d
Carter GT.Nietsche JA.Goodman JJ.Torrey MJ.Dunne TS.Siegel MM.Borders DB. J. Chem. Soc., Chem. Commun. 1989, 1271 -
3a
Müller K.Leukel P.Ziereis K.Gawlik I. J. Med. Chem. 1994, 37: 1660 -
3b
Barton DHR.Challis JA.Magnus PD.Marshall JP. J. Chem. Soc. C 1971, 2241 -
4a
Buchta E.Egger H. Chem. Ber. 1957, 90: 2760 -
4b
Shiue J.-S.Lin M.-H.Fang J.-M. J. Org. Chem. 1997, 62: 4643 -
4c
Chan TH.Brownbridge P. J. Am. Chem. Soc. 1980, 102: 3534 -
4d
Lee SD.Chan TH. Tetrahedron 1984, 40: 3611 -
4e
Kang GJ.Chan TH. J. Org. Chem. 1985, 50: 452 -
4f For the synthesis of salicylic derivatives
by reactions of 1,3-dicarbonyl dianions, see for example:
Harris TM.Wittek PJ. J. Am. Chem. Soc. 1975, 97: 3270 -
4g For the reaction of dimethyl
1,3-acetonedicarboxylate with alkynals and alkynones, see:
Covarrubias-Zúniga A.Ríos-Barrios E. J. Org. Chem. 1997, 62: 5688 ; and references cited therein - For reviews of domino reactions, see:
-
5a
Tietze LF.Beifuss U. Angew. Chem., Int. Ed. Engl. 1993, 32: 131 ; Angew. Chem. 1993, 105, 137 -
5b
Tietze LF. Chem. Rev. 1996, 96: 115 - For related cyclization reactions of 3-formylchromones, see:
-
6a
Nohara A.Umetani T.Sanno Y. Tetrahedron 1974, 30: 3553 -
6b
Jones WD.Albrecht WL. J. Org. Chem. 1976, 41: 706 -
6c The cyclization of 3-formyl-chromones
with formamidine and amidines afforded 5-(2-hydroxybenzoyl)-pyrimidines:
Löwe W. Synthesis 1976, 274 -
6d See also:
Petersen U.Heitzer H. Liebigs Ann. Chem. 1976, 1663 -
6e With enamines:
Heber D. Synthesis 1978, 691 -
6f With hydrazines:
Eiden F.Haverland H. Arch. Pharm. (Weinheim, Ger.) 1968, 301: 819 -
6g See also:
Ghosh CK.Mukhopadhyay KK. J. Ind. Chem. Soc. 1978, 55: 386 -
6h With H2NOH·HCl:
Hsung RP.Zificsak CA.Wei L.-L.Zehnder LR.Park F.Kim M.Tran T.-TT. J. Org. Chem. 1999, 64: 8736 -
6i With o-phenylenediamine:
Ghosh CK.Khan S. Synthesis 1980, 701 -
6j For conversions into pyrroles
and thiophenes:
Fitton AO.Frost JR.Suschitzky H.Hougton PG. Synthesis 1977, 133 -
6k For a review on 3-formylchromones,
see:
Ellis GP. Heterocyclic Compounds Vol. 35:Weisberger A. Wiley-Interscience; New York: 1977. p.921 - For phosphorane 3b, see:
-
7a
Hatanaka M.Tanaka Y.Ueda I. Tetrahedron Lett. 1995, 3719 -
7b
Banwell MG.Cameron JM. Tetrahedron Lett. 1996, 525 -
7c
Hatanaka M.Ishida A.Tanaka Y.Ueda I. Tetrahedron Lett. 1996, 401 -
7d
Ceccarelli S.Piarulli U.Gennari C. Tetrahedron Lett. 1999, 153 -
8a
Ghosh CK.Khan S. Synthesis 1981, 903 -
8b
Hass G.Stanton JL.von Sprecher A.Wenk P. J. Heterocycl. Chem. 1981, 18: 607 -
8c
Prousek J. Collect. Czech. Chem. Commun. 1991, 1361 -
8d
Ghosh CK.Bandyopadhyay C.Biswas S.Chakravarty AK. Ind. J. Chem., Sect. B 1990, 29: 814 -
8e
Bandyopadhyay C.Sur KR.Patra R. J. Chem. Res., Synop. 1998, 12: 802
References
Representative Experimental Procedure: A THF suspension (5 mL) of NaH (78 mg, 3.25 mmol) and 3b (556 mg, 1.43 mmol) was stirred under nitrogen atmosphere at 0 °C for 30 min. A THF solution (10 mL) of 2a (190 mg, 1.1 mmol) was added and the solution was stirred for 60 min at 0 °C. The reaction mixture was refluxed for 24 h, cooled and subsequently stirred for 12 h at 20 °C. To the mixture was added diethyl ether (30 mL), an aqueous solution of HCl (5 mL, 1 M) and a saturated solution of NaCl. The aqueous layer was separated and extracted with CH2Cl2 (3 × 10 mL). The combined organic layers were dried (MgSO4), filtered and the solvent of the filtrate was removed in vacuo. The residue was purified by column chromatography (silica gel, diethyl ether/petroleum ether = 1:20) to give 4b (52%) as a yellow solid. Spectroscopic data of 4b: 1H NMR (CDCl3, 250 MHz): δ = 1.42 (t, 3 J = 7 Hz, 3 H, CH3), 4.45 (q, 3 J = 7 Hz, 2 H, OCH 2CH3), 6.91 (dd, 3 J 1 = 7 Hz, 3 J 2 = 8 Hz, 1 H, Ar), 7.08 (d, 3 J = 8 Hz, 1 H, Ar), 7.10 (d, 3 J = 8 Hz, 1 H, Ar), 7.53 (dd, 3 J 1 = 7 Hz, 3 J 2 = 8 Hz, 1 H, Ar), 7.59 (d, 3 J = 8 Hz, 1 H, Ar), 7.84 (d, 3 J = 8 Hz, 1 H, Ar), 8.30 (s, 1 H, Ar), 11.34 (s, 1 H, OH), 11.87 (s, 1 H, OH). 13C NMR (CDCl3, 50 MHz): δ = 14.15 (CH3), 62.07 (CH2), 112.47, 119.03, 129.00 (C, Ar, ortho and para to OH), 117.74, 118.51, 118.70 (CH, Ar, ortho and para to OH), 132.36, 132.95, 136.18, 136.59 (CH, Ar, meta to OH), 163.00, 164.70, 169.61 (C, C-OH, CO2Et), 199.12 (C, CO). IR (KBr): 3178 (w), 3059 (w), 2987 (w), 2933 (w), 1683 (s), 1629 (s), 1589 (s), 1467 (m), 1444 (m), 1397 (m), 1343 (s), 1293 (s), 1262 (s), 1242 (s), 1176 (m), 1084 (m) cm-1. MS (70 eV): m/z (%) = 286 (100) [M+], 121(94). Anal. Calcd for C16H14O5: C, 67.31; H, 4.93. Found: C, 66.88; H, 5.18. All compounds gave satisfactory spectroscopic and analytical and/or high resolution mass data.