Abstract
Catalyzed by DBU or DBN, 2-acetoxy benzofuranones and 2-acetoxy-N-Tos indolin-3-ones, were readily prepared from o-acyl phenols and o-acyl anilines, respectively, reacted with H2O or a range of amines to afford o-OH and o-NH-Tos benzoic acids or benzoamides in moderate to excellent yields.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Lszló K, Barbara C (2005) Strategic application of named reaction in organic synthfcesis. Elsevier Inc, London
Hamlin KE, Weston AW (2011) The Cleavage of non-enolizable ketones with sodium amide. The Haller-Bauer reaction. Org React 1–36. doi:10.1002/0471264180.or009.01
Paquette LA, Gilday JP (1990) Carbon–carbon bond cleavage by the Haller–Bauer and related reactions: a review. Org Prep Proceed Int 22: 167–201. doi:10.1080/00304949009458195
Mehta G, Venkateswaran RV (2000) Haller–Bauer reaction revisited: synthetic applications of a versatile C–C bond scission reaction. Tetrahedron 56: 1399–1422. doi:10.1016/S0040-4020(99)00921-7
Ishihara K, Yano T (2004) Synthesis of carboxamides by LDA-catalyzed Haller–Bauer and Cannizzaro reactions. Org Lett 6: 1983–1986. doi:10.1021/ol0494459
Wei Y, Liu J, Lin S et al (2010) Acetoacetanilides as masked isocyanates: facile and efficient synthesis of unsymmetrically substituted ureas. Org Lett 12: 4220–4223. doi:10.1021/ol101474f
Cao L, Ding J, Gao M et al (2009) Novel and direct transformation of methyl ketones or carbinols to primary amides by employing aqueous ammonia. Org Lett 11: 3810–3813. doi:10.1021/ol901250c
Cho-Schultz S, Patten MJ, Huang B et al (2009) Solution-phase parallel synthesis of Hsp90 inhibitors. J Comb Chem 11: 860–874. doi:10.1021/cc900056d
Li X, Hewgley B, Mulrooney CA et al (2003) Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-dizadecalin metal complexes: efficient formation of chiral functionalized BINOL derivatives. J Org Chem 68: 5500–5511. doi:10.1021/jo0340206
Bader AR, Kontowicz AD (1953) Phenyl ester. J Am Chem Soc 75: 5416. doi:10.1021/ja01117a504
Katritzky AR, Singh SK, Cai C et al (2006) Direct synthesis of esters and amides from unprotected hydroxyaromatic and -aliphatic carboxylic acids. J Org Chem 71: 3364–3374. doi:10.1021/jo052293q
Balduzzi G, Bigi F, Casiraghi G et al (1982) Unusual friedel-crafts reactions: synthesis of salicylanilides via ortho-aminocarbonylation of phenols with phenyl isocyanate. Synthesis 7: 879–881. doi:10.1055/s-1982-29987
Fu JM, Sharp MJ, Snieckus V (1988) The directed ortho metalation connection to aryl-aryl cross coupling: a general regiospecific synthesis of phenanthrols. Tetrahedron Lett 29: 5459–5462. doi:10.1016/S0040-4039(00)80786-8
Kamila S, Mukherjee C, Mondal SS et al (2003) Application of directed metallation in synthesis. Part 3. Studies in the synthesis of (±)-semivioxanthin and its analogues. Tetrahedron 59: 1339–1348. doi:10.1016/S0040-4020(02)01599-5
O’Mahony G, Pitts AK (2010) Synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups. Org Lett 12: 2024–2027. doi:10.1021/ol100507n
Surman MD, Mulvihill MJ, Miller MJ (2002) Novel, 1,4-benzodiazepines from acylnitroso-derived hetero-diels-alder cycloadducts. Org Lett 4: 139–141. doi:10.1021/ol017036w
Banfi L, Basso A, Guanti G et al (2007) Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: convergent multicomponent synthesis of 1-sulfonyl 1,4-diazepan-5-ones and of their benzo-fused derivatives. J Org Chem 72: 2151–2160. doi:10.1021/jo062626z
Peifer C, Kinkel K, Abadleh M et al (2007) From five- to six-membered rings: 3,4-diarylquinolinone as lead for novel p38MAP kinase inhibitors. J Med Chem 50: 1213–1221. doi:10.1021/jm061097o
Gilleron P, Wlodarczyk N, Houssin R et al (2007) Design, synthesis and biological evaluation of substituted dioxodibenzothiazepines and dibenzocycloheptanes as farnesyltransferase inhibitors. Bioorg Med Chem Lett 17: 5465–5471. doi:10.1016/j.bmcl.2007.07.002
Xue H, Lu X, Zheng P et al (2010) Highly suppressing wild-type HIV-1 and Y181C mutant HIV-1 strains by 10-chloromethyl-11-demethyl-12-oxo-calanolide A with druggable profile. J Med Chem 53: 1397–1401. doi:10.1021/jm901653e
Ma T, Liu L, Xue H et al (2008) Chemical library and structure–activity relationships of 11-demethyl-12-oxo calanolide A analogues as Anti-HIV-1 agents. J Med Chem 51: 1432–1446. doi:10.1021/jm701405p
Ma T, Gao Q, Chen Z et al (2008) Chemical resolution of (±)-calanolide A, (±)-cordatolide A and their demethyl analogues. Bioorg Med Chem Lett 11(18): 1079–1083. doi:10.1016/j.bmcl.2007.12.008
Flavin MT, Rizzo JD, Khilevich A et al (1996) Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-Calanolide A and its enantiomers. J Med Chem 39: 1303–1313. doi:10.1021/jm950797i
Fan R, Sun Y, Ye Y (2009) Iodine(III)-mediated tandem acetoxylation-cyclization of o-acyl phenols for the facile construction of α-acetoxy benzofuranones. Org Lett 11: 5174–5177. doi:10.1021/ol902067x
Sun Y, Fan R (2010) Construction of 3-oxyindoles via hypervalent iodine mediated tandem cyclization–acetoxylation of o-acyl anilines. Chem Commun 46: 6834–6836. doi:10.1039/C0CC01911A
Author information
Authors and Affiliations
Corresponding author
Electronic Supplementary Material
The Below is the Electronic Supplementary Material.
Rights and permissions
About this article
Cite this article
Zheng, P., Lu, S. & Liu, G. An unexpected C–C cleavage reaction: new and mild access to o-OH and o-NH-Tos benzoic acids or benzoamides. Mol Divers 15, 971–977 (2011). https://doi.org/10.1007/s11030-011-9329-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-011-9329-y