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

References

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