A Facile Synthesis of (E,Z)-3-Chloro-2-propenamides, Acids, and Esters from 2,3-Acetylenic Acids with Oxalyl Chloride in DMF

Synthetic Communications

Volumn 34, Issue 4, 2004, Pages 657-664

  Urdaneta, Neudo A ^a   Salazar, José ^a   Herrera, Julio C ^a   López, Simón E ^a  

^a UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

2,3 Acetylenic acids; 3 Chloro 2 alkenoic acids; DMF; Hydrochlorination; Oxalyl chloride

Indexed keywords

2,3 ACETYLENIC ACID; 3 CHLORO 2 BUTENOIC ACID; 3 CHLORO 3 PHENYL 2 PROPENOIC ACID; 3 CHLORO 3 PHENYL N PIPERIDYL 2 PROPENAMIDE; 3 CHLORO 3 PHENYL N PYRROLIDYL 2 PROPENAMIDE; 3 CHLORO 3 PHENYL N,N DIETHYL 2 PROPENAMIDE; 3 CHLORO 3 PHENYL N1 PHENYLETHYL 2 PROPENAMIDE; 3 CHLORO N PYRROLIDYL 2 BUTENAMIDE; 3 CHLOROPROPENOIC ACID; ACETYLENE DERIVATIVE; ACID; ACRYLIC ACID DERIVATIVE; ALCOHOL; AMINE; BENZENE DERIVATIVE; CHLORINE DERIVATIVE; ESTER; ETHYL 3 CHLORO 3 PHENYL 2 PROPENAMIDE; OXALYL CHLORIDE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; SYNTHESIS;

EID: 1542530875     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120027713     Document Type: Article

References (21)

1. Urdaneta, N.; Herrera, J.C.; Salazar, J.; López, S.E. Hydrochlorination of 2,3-acetylenic acids with thionyl chloride in DMF. Synth. Commun. 2002, 32 (19), 3003-3009.
2. Abarbri, M.; Parrain, J.L.; Citrat, J.C.; Duchéne, A. Efficient synthesis of conjugated (2E) or (2Z)-en-4-ynoic acids and (2E,4E)- or (2Z,4E)-dienoic acids via palladium-catalyzed cross-coupling. Synthesis 1996, 7, 82-86.
3. Prié, G.; Thibonnet, J.; Abarbri, M.; Duchéne, A.; Parrain, J.L. A stereoselective access to functional dienes containing a trifluormethyl group via still cross-coupling of ethyl 4,4,4-trifluoro-3-iodobutenoate. Synlett. 1998, 7, 839-840.
4. Takeuchi, R.; Tanabe, K.; Tanaka, S. Stereodivergent synthesis of (E)- and Z(Z)-2-alken-4-yn-1-ols from 2-propynoic acid: a practical route via 2-alken-4-ynoates. J. Org. Chem. 2000, 65, 1558-1561.
5. Amino, Y.; Kanada, K.; Tol, K.; Kumashiroa, K.; Fukushima, K. Phenylalanine derivatives enhancing intestinal absorption of insuline in mice. Chem. Pharm. Bull. 1988, 36, 4426-4434.
6. Latif, Z.; Hartley, T.G.; Rice, M.J.; Waigh, R.D.; Waterman, P.G. Novel and insecticidal isobutylamides from Dinosperma reythrococca. J. Nat. Prod. 1998, 61, 614-617.
7. Alécio, A.C.; Bolzani, V.Da.S.; Young, M.C.M.; Kato, M.J.; Furlan, M. Antifungal amide from leaves of Piper hispidum. J. Nat. Prod. 1998, 61, 637-639.
8. Junior, J.X.; de Duarte, A.C.M.; Chaves, M.C.; de Parente, J.P.; Fraga, C.A.M.; Barreiro, E.J. Synthesis of natural amide alkaloid piperdardine and a new bioactive analogue. Synth. Commun. 2001, 28, 117.
9. Song, Y.; Clizbe, L.; Bhakta, C.; Teng, W.; Li, W.; Wong, P.; Huang, B.; Sinho, U.; Park, G.; Reed, A.; Scarborough, R.M. Substituted acrylamides as factor Xa inhibitors: improving bioavailability by P1 modification. Bioorg. Med. Chem. Lett. 2002, 12, 2043-2045.
10. Fieser, M.; Fieser, L. Reagents for Organic Synthesis; John Wiley & Sons: New York, 1967; 286-287.
11. Stack, D.P.; Coates, R.M. Preparation of β-haloacryloyl chlorides. Synthesis 1984, 434-435.
12. Ma, S.; Lu, L. Differentiation of the reactivities of carbon-carbon multiple bonds in one molecule. Highly chemo- and stereoselective hydrohalogenation of allyl propargyl propiolates. Tetrahedron Lett. 1990, 31, 7653-7656.
13. Ma, S.; Lu, X.; Li, Z. A novel regio- and stereospecific hydrohalogenation reaction of 2-propynoic acids and its derivatives. J. Org. Chem. 1992, 57, 709-713.
14. Urdaneta, N.; Herrera, J.C.; Rodriguez, E.N. Synthesis and geometric assignment for (Z,E)-3-yodo-3-methyl-propenoic and (E) -3-halo-3-phenyl-propenoic acids. Ciencia 1995, 3, 41. Chem. Abstr. 123, 338779.
15. Urdaneta, N.; Herrera, J.C.; Rodriguez, E.N. Synthesis and geometric assignment for (Z,E)-3-yodo-3-methyl-propenoic and (E) -3-halo-3-phenyl-propenoic acids. Ciencia 1995, 3, 41. Chem. Abstr. 123, 338779.
16. Le Noble, W.J. The configuration of some substituted β-haloacrylic acids. J. Am. Chem. Soc. 1961, 83, 3897-3899.
17. (a) Mavrov, M.V.; Urdaneta, N.A.; Serebryakov, E.P. Configurational assignments in 3-bromo-2-butenoic acids. Bull. Chem. Soc. SSSR (Engl. Trans.) 1989, 38, 1289-1292;
18. (b) Mavrov, M.V.; Urdaneta, N.A.; Serebryakov, E.P. Configurational assignments in 3-bromo-2-buetoic acids. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 1409-1412. Chem. Abstr. 112, 76346u.
19. (b) Mavrov, M.V.; Urdaneta, N.A.; Serebryakov, E.P. Configurational assignments in 3-bromo-2-buetoic acids. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 1409-1412. Chem. Abstr. 112, 76346u.
20. Jalander, M.; Broms, M. Stereochemistry of the reactions of Cu I catalyzed Grignard reagents with ethyl (E)- and (Z)-β-chlorocinnamates. Acta Chem. Scand. 1983, B37, 173.
21. Braveman, M.; Cherkinsky, E.V.K.; Suresh-Kumar, H.; Gottlieb, E.H. Rearrangements of trihalomethyl ketones. Tetrahedron 2000, 56, 4521-4529.