Sigmatropic rearrangement of ammonium ylideskey step in the synthesis of methyl 2-formylphenyl acetate

Synthetic Communications

Volumn 41, Issue 22, 2011, Pages 3308-3317

  Kowalkowska, Anna ^a   Jończyk, Andrzej ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Ammonium salts; ammonium ylides; methyl 2 formylphenyl acetate; sigmatropic rearrangement

Indexed keywords

2 (METHOXYCARBONYMETHYL)ALPHA(DIMETHYLAMINO)PHENYLACETONITRILE; 3 CYANO 3 DIMETHYLAMINO 2 PHENYLPROPIONIC ACID METHYL ESTER; ACETIC ACID DERIVATIVE; AMMONIUM DERIVATIVE; METHYL 2 FORMYLPHENYL ACETATE; METHYL ALPHA(N CYANOMETHYL N METHYLAMINO)PHENYLACETATE; METHYL ALPHA(N METHYLAMINO)PHENYLACETATE; METHYL ALPHA(N,N DIMETHYLAMINO)PHENYLACETATE; N CYANOMETHYL N,N DIMETHYL N(ALPHA METHOXYCARBONYL)BENZYLAMMONIUM BROMIDE; N CYANOMETHYL N,N DIMETHYL N(ALPHA METHOXYCARBONYL)BENZYLAMMONIUM METHYLSULFATE; N CYANOMETHYL N,N DIMETHYL N(ALPHA METHOXYCARBONYL)BENZYLAMMONIUM SALT; N CYANOMETHYL N,N DIMETHYL N(ALPHA METHOXYCARBONYL)BENZYLAMMONIUM TETRAFLUOROBORATE; N CYANOMETHYL N,N DIMETHYL N(ALPHA METHOXYCARBONYL)BENZYLAMMONIUM TRIFLUOROMETHANESULFONATE; UNCLASSIFIED DRUG;

ARTICLE; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 79960903120     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.517891     Document Type: Article

References (19)

1. Wildeman, J.; Borgen, P. C.; Pluim, H.; Rouwette, P. H. F. M.; van Leusen, A. M. Synthesis of naphthalenes from ortho-substituted benzyl sulfones and Michael acceptors. Tetrahedron Lett. 1978, 25, 2213-2216.
2. Tyrała, A.; Makosza, M. Simple synthesis of 2-nitronaphthalene derivatives from substituted p-nitrobenzyl sulfones. Synthesis 1994, 264-266. (Pubitemid 24122763)
3. Jonczyk, A.; Panasiewicz, M.; Zdrojewski, T. The synthesis of 2-cyanomethylbenzaldehyde, useful substrate for construction of fused ring compounds. Synth. Commun. 2003, 33, 4095-4100. (Pubitemid 37494368)
4. Panasiewicz, M.; Zdrojewski, T.; Chrulski, K.; Wojtasiewicz, A.; Jonczyk, A. 2-Cyanomethylbenzaldehyde, useful substrate for preparation of some 1,3-and 1,2,3-trisubstituted naphthalenes or substituted 1-cyanobenzobicyclo[2.2.2] octenes. Arkivoc, 2009, (1), 1-13.
5. Zdrojewski, T.; Jonczyk, A. A general approach to 3-aminoisoquinolines, its N-monoand N,N-disubstituted derivatives. Tetrahedron 1995, 51, 12439-12444.
6. Akbutina, F. A.; Davydova, V. A.; Zarudii, F. A.; Sagitdinov, I. A.; Miftakhov, M. S. Prostanoids, part LXX: Synthesis and study of antiinflammatory and antiulcerogenic activity of 2-(3-hydroxy-1E-octenyl)phenylacetic acid methyl ester. Pharm. Chem. J. 1998, 32, 255-257. (Pubitemid 128708197)
7. Miftakhov, M. S.; Akbutina, F. A.; Tolstikov, A. G.; Anpilogov, A. P.; Tolstikov, G. A. Prostanoids, XXI: Synthesis of a-pentanorbenzo analogs of prostaglandins. Zh. Org. Khim. 1987, 23, 2559-2564.
8. Lee, H.-K.; Kim, H.-R.; Tomioka, H. A convenient method for the synthesis of 1,3-bis(diazo)-2-indanone and its photochemistry in methanol at room temperature. Bull. Korean Chem. Soc. 1988, 9, 399-400.
9. Murata, S.; Yamamoto, T.; Tomioka, H. Photochemistry of 1,3-bis(diazo)indan-2-one: Consecutive decomposition and suppression of a Wolff rearrangement. J. Am. Chem. Soc. 1993, 115, 4013-4023.
10. Jung, M. E.; Brown, R. W.; Hagenah, J. A.; Strouse, C. E. Cycloadditions of benzopyrones: Rapid access to bicyclic ab-ring analogues of anthracyclines. Tetrahedron Lett. 1984, 25, 3659-3662.
11. Bleasdale, D. A.; Jones, D. W. 2-Benzopyran-3-ones as synthetic building blocks: Regioselective Diels-Alder additions with simple olefins leading to aromatic steroids. J. Chem. Soc., Perkin Trans. 1 1991, 1683-1692.
12. Belanger, G.; April, M.; Dauphin, E .; Roy, S. Effect of substitution on the intramolecular 1,3-dipolar cycloaddition of alkene tethered munchnones. J. Org. Chem. 2007, 72, 1104-1111.
13. Davtyan, S. M.; Papayan, G. L.; Asratyan, S. N. Derivatives of c-aminobutyric acid, I: Synthesis of methyl esters of N-substituted a-phenylaminoacetic acids and products of their reduction. Arm. Khim. Zh. 1970, 23, 251-257.
14. Duhamel, L.; Duhamel, P.; Siret, P. Synthèse des a-aminoaldehydes par reduction d'a-aminoesters et d'a-aminoamides. Bull. Soc. Chim. Fr. 1973, 2460-2466.
15. Meyer, E.; Joussef, A. C.; Gallardo, H.; de Souza, L. de B. P. Synthesis of a new 4,5-dihydro-3(2H)-pyridazinone derivatives. Synth. Commun. 2004, 34, 783-793.
16. Tomioka, H.; Suzuki, K. Formal activation of C-H bonds toward carbenes by captodative substituents. Tetrahedron Lett. 1989, 30, 6353-6356. (Pubitemid 19280225)
17. Yoffe, S. T.; Pietrovskii, P. V.; Fedin, E. I.; Vatsuro, K. V.; Burenko, P. S.; Kabachnik, M. I. The kinetic investigation of trans-aldo-cis-enol transformation of alkyl 2-formyl-2-phenylacetates. Tetrahedron Lett. 1967, 4525-4528.
18. Gordon, E. M.; Pluscc, J. Oxidation of a-amino ester: One-step synthesis of sulfenimines. J. Org. Chem. 1979, 44, 1218-1221.
19. Pine, S. H. The base-promoted rearrangements of quaternary ammonium salts. Org. React. 1970, 18, 403-464.