2-Diethoxyphosphoryl-4-nitroalkanoates - Versatile intermediates in the synthesis of α-alkylidene-γ-lactones and lactams

Synlett

Volumn , Issue 15, 2004, Pages 2685-2688

  Błaszczyk, Edyta ^a   Krawczyk, Henryk ^a   Janecki, Tomasz ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

alkylidenelactones; methylidenelactams; Michael addition; Nitroalkanoates; Wittig type olefination

Indexed keywords

2 PYRROLIDONE DERIVATIVE; 3 (DIETHOXYPHOSPHORYL)PYRROLIDIN 2 ONE; 3 (DIETHOXYPHOSPHORYL)TETRAHYDRO 2 FURANONE; 3 METHYLIDENEPYRROLIDIN 2 ONE; ACRYLIC ACID DERIVATIVE; ALKANE DERIVATIVE; ALKANOIC ACID; ETHYL (2 DIETHOXYPHOSPHORYL)ACRYLATE; FURANONE DERIVATIVE; LACTAM; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HORNER WADSWORTH EMMONS REACTION; MICHAEL ADDITION; OLEFINATION; REACTION ANALYSIS; SYNTHESIS;

EID: 10844281771     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-835656     Document Type: Article

References (16)

1. Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
2. Paquette, L. A.; Mendez-Andino, J. Tetrahedron Lett. 1999, 40, 4301; and references cited therein.
3. Steurer, S.; Podlech, J. Eur. J. Org. Chem. 2002, 899; and references cited therein.
4. Kang, S.-K.; Kim, K.-J.; Hong, Y.-T. Angew. Chem. Int. Ed. 2002, 1584; and references cited therein.
5. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
6. Bauchet, R.; Le Rouille, E.; Foucaud, A. Bull. Soc. Chim. Fr. 1991, 128, 267.
7. Ballini, R.; Bosica, G.; Livi, D. Synthesis 2001, 1519.
8. Basavaiah, D.; Rao, J. S. Tetrahedron Lett. 2004, 45, 1621.
9. Janecki, T.; Błaszczyk, E. Synthesis 2001, 403.
10. 4 (3 mL) was added to the residue which was distilled in high vacuum (85-87 °C/0.4 Torr) to give pure ethyl 2-(diethoxyphosphory)lacrylate (6, 22.4 g; 73%). (b) Semmelhack, M. F.; Tomesh, J. C.; Czarny, M.; Boettger, S. J. Org. Chem. 1978, 43, 1259.
11. 4 (3 mL) was added to the residue which was distilled in high vacuum (85-87 °C/0.4 Torr) to give pure ethyl 2-(diethoxyphosphory)lacrylate (6, 22.4 g; 73%). (b) Semmelhack, M. F.; Tomesh, J. C.; Czarny, M.; Boettger, S. J. Org. Chem. 1978, 43, 1259.
12. 9P: C, 51.00; H, 6.76; N, 3.13; P, 6.92. Found: C, 51.12; H, 6.69; N, 3.20; P, 6.80.
13. Villieras, J.; Rambaud, M. Synthesis 1984, 406.
14. 4: C, 67.73; H, 6.50. Found: C, 67.88; H, 6.41.
15. 3: C, 66.94; H, 6.48; N, 6.00. Found: C, 67.09; H, 6.57, N, 5.83.
16. Macomber, R. S. A. Complete Introduction to Modern NMR Spectroscopy; John Wiley and Sons: New York, 1998, 416.