Reaction between triphenylphosphine and acetylenic esters or acetylenic ketones in the presence of mercaptoesters

Synthetic Communications

Volumn 39, Issue 19, 2009, Pages 3482-3492

  Mosslemin, Mohammad H ^a   Anary Abbassinejad, Mohammad ^a   Hassanabadi, Alireza ^a   Mohebat, Marzieh ^a   Nateghi, Mohammad R ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Acetylenic esters; Acetylenic ketones; Mercaptoesters; Substituted furans; Triphenylphosphine

Indexed keywords

ACETIC ACID DERIVATIVE; ESTER DERIVATIVE; ETHYL (1 BENZOYL 3 OXO 3 PHENYLPROPENYLSULFANYL)ACETATE; ETHYL (1 BENZOYL 3 OXO 3 PHENYLPROPYLSULFANYL)ACETATE; ETHYL (2,5 DIPHENYL FURAN 3 YL SULFANYL)ACETATE; FURAN DERIVATIVE; KETONE DERIVATIVE; SULFIDE; THIOESTER; THIOL DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 70349224462     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902778027     Document Type: Article

References (12)

1. Corbridge, D. E. C. Phosphorus: An Outline of the Chemistry, Biochemistry, and Uses, 5th ed.; Elsevier: Amsterdam, 1995.
2. Yavari, I.; Adib, M.; Hojabri, L. Vinyltriphenylphosphonium salt-mediated serendipitous synthesis of aryliminophosphoranes. Tetrahedron 2002, 58, 7213.
3. Engel, R. Synthesis of Carbon-Phosphorus Bonds; CRC Press: Boca Raton, FL, 1988.
4. Trost, B. M.; Dake, G. R. Nucleophilic a-addition to alkynoates: A synthesis of dehydroamino acids. J. Am. Chem. Soc. 1997, 119, 7595.
5. Nair, V.; Nair, J. S.; Vinod, A. U.; Rath, N. P. Triphenylphosphine- promoted addition of dimethyl acetylenedicarboxylate to 1,2-benzoquinones: Facile synthesis of novel c-spirolactones. J. Chem. Soc., Perkin Trans. 1 1997, 3129.
6. Yavari, I.; Hekmat-Shoar, R.; Zonouzi, A. A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt. Tetrahedron Lett. 1998, 39, 2391.
7. Yavari, I.; Adib, M.; Hojabri, L. Vinyltriphenylphosphonium salt-mediated synthesis of functionalized coumarins. Tetrahedron 2001, 57, 7537.
8. Anary-Abbasinejad, M.; Rostami, N.; Parhami, A.; Hassanabadi, A. Synthesis of functionalised phosphonates by three-component reaction between phosphites, dialkyl acetylenedicarboxylates, and pyrrole, indole, or benzo-triazole. J. Chem. Res. 2007, 291.
9. Anary-Abbasinejad, M.; Hassanabadi, A.; Anaraki-Ardakani, H. One-pot synthesis of stable phosphite ylides by three-component reaction between acetylenic esters, aldehyde semicarbazones, and tributyl-or triethyl phosphite. J. Chem. Res. 2007, 455.
10. Anaraki-Ardakani, H.; Sadeghian, S.; Rastegari, F.; Hassanabadi, A.; Anary-Abbasinejad, M. Three-component reaction of triphenylphosphine, acetylenic esters, and arylsulfonyl hydrazides or arylhydrazines: An efficient one-pot synthesis of stable b-nitrogen-substituted phosphorus ylides. Synth. Commun. 2008, 38 (12), 1990.
11. Anary-Abbasinejad, M.; Anaraki-Ardakani, H.; Hosseini-Mehdiabad, H. One-pot synthesis of stable phosphorus ylides by three-component reaction between dimethyl acetylenedicarboxylate, semicarbazones, and triphenylpho-sphine. Phosphorus, Sulfur Silicon Relat.Elem. 2008, 183 (6), 1440.
12. Eliel, E. L.; Wilen, S. H.; Mander, L. N. In Stereochemistry of Organic Compounds; Wiley: New York, 1994; p. 569.