Superoxide ion induced oxidation of γ-lactones to γ-ketocarboxylic acids

Synthetic Communications

Volumn 34, Issue 24, 2004, Pages 4471-4475

  Singh, S ^a   Verma, M ^b   Singh, K N ^b  

^a BUNDELKHAND INSTITUTE OF ENGINEERING AND TECHNOLOGY   (India)

^b BANARAS HINDU UNIVERSITY   (India)

Author keywords

Ketocarboxylic acids; Lactones; Phase transfer catalyst; Superoxide

Indexed keywords

ALPHA METHYL GAMMA BUTYROLACTONE; CARBOXYLIC ACID DERIVATIVE; DICARBOXYLIC ACID; GAMMA BUTYROLACTONE; GAMMA CAPROLACTONE; GAMMA DECANOLACTONE; GAMMA KETOCARBOXYLIC ACID DERIVATIVE; GAMMA LACTONE DERIVATIVE; GAMMA OCTANOIC LACTONE; GAMMA PHENYLLACTONE; GAMMA VALEROLACTONE; SUPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 11244272957     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200043177     Document Type: Article

References (13)

1. Suzuki, K.; Senoh, A.; Ueno, K. Simple synthesis of ring-fused pyridazin-3-ones. Heterocycles 2002, 57 (4), 723-732.
2. Chen, Y.T.; Seto, C.T. Divalent and trivalent α-ketocarboxylic acids as inhibitors of protein tyrosine phosphatases. J. Med. Chem. 2002, 45 (18), 3946-3952.
3. Ramachandran, P.V.; Pitre, S.; Brown, H.C. Selective reductions. 59. Effective intramolecular asymmetric reductions of α-, β-, and γ-keto acids with diisopinocampheylborane and intermolecular asymmetric reductions of the corresponding esters with B-chlorodiisopinocampheylborane. J. Org. Chem. 2002, 67 (15), 5315-5319.
4. Simchen, G.; Siegl, G. Reactions of trialkylsilyl trifluoromethane- sulfonates XI. Synthesis of α-oxocarboxylic acid derivatives from 2-O-functionalized trimethylsilyl ketene acetals. Liebigs Ann. Chem. 1992, 6, 607-614.
5. Kim, S.-J.; Kang, H.-Y.; Sherman, D.H. Synthesis of triketide δ-lactones. Synthesis 2001, 12, 1790-1793.
6. Valla, A.; Andriamialisoa, Z.; Zentz, F.; Prat, V.; Laurent, A.; Giraud, M. Synthesis of new γ- and σ-lactones by acid cyclization of 2,4-diethylenicdiacids. Synth. Commun. 2001, 31 (2), 279-282.
7. Rayabarapu, D.K.; Cheng, C.-H. Synthesis of seven-membered lactones via nickel- and zinc-catalyzed highly regio- and stereoselective cyclization of 2-Iodobenzyl alcohols with propiolates. J. Amer. Chem. Soc. 2002, 124 (20), 5630-5631.
8. Schneider, C. Catalytic, enantioselective synthesis of β-lactones - versatile synthetic building blocks in organic chemistry. Angew. Chem. Int. Ed. 2002, 41 (5), 744-746.
9. Greatrex, B.W.; Kimber, M.C.; Taylor, D.K.; Fallen, G.; Tiekink, E.R.T. 1,2-Dioxines as masked cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones. J. Org. Chem. 2002, 67 (15), 5307-5314.
10. Franck, X.; Figadere, B. Synthesis of acaterin via a new application of the Baylis-Hillman reaction. Tetrahedron Lett. 2002, 43 (8), 1449-1452.
11. Shukla, A.K.; Singh, S.; Singh, K.N. Henry and Knoevengel type condensation reactions initiated by tetraethylammonium superoxide in aprotic medium. Indian J. Chem. 2001, 40B, 391-393.
12. Kumar, R.; Singh, K.N. Tetraethylammonium bromide catalysed phase transfer reaction of potassium superoxide with hydrazones and tosylhydrazones. Indian J. Chem. 2001, 40B, 579-583.
13. Singh, K.N.; Singh, S. Reaction of electrogenerated superoxide ion with compounds having labile hydrogens. Bull. Electrochem. 2000, 16, 385-387.