Efficient methods for the synthesis of arylacetonitriles

Synthesis

Volumn , Issue 19, 2010, Pages 3332-3338

  Stazi, Federica ^a   Maton, William ^a   Castoldi, Damiano ^a   Westerduin, Pieter ^a   Curcuruto, Ornella ^a   Bacchi, Sergio ^a  

^a GSK   (Italy)

Author keywords

Decarboxylations; Nitriles; Nucleophilic aromatic substitutions; Reductions; Wittig reactions

Indexed keywords

DECARBOXYLATIONS; EFFICIENT METHOD; ELECTRON-DEFICIENT; NITRILES; NUCLEOPHILIC AROMATIC SUBSTITUTION; TRIFLUOROMETHYL; WITTIG REACTION;

ACETONITRILE; AROMATIC COMPOUNDS; CYANIDES;

CARBOXYLATION;

(METHOXYMETHYL)(TRIPHENYL)PHOSPHONIUM CHLORIDE; [2 FLUORO 4 (TRIFLUOROMETHYL)PHENYL]ACETONITRILE; ACETONITRILE DERIVATIVE; ALDEHYDE; HYDROCHLORIC ACID; POTASSIUM CYANIDE; POTASSIUM HEXAMETHYLDISILAZIDE; REAGENT; SODIUM BOROHYDRIDE; TETRAHYDROFURAN; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DECARBOXYLATION; HYDROLYSIS; ISOMER; REDUCTION; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77956527233     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1257871     Document Type: Article

References (26)

1. Lwowski W, In 1,3-Dipolar Cycloaddition Chemistry Padwa A Wiley New York 1984 Vol. 1
2. Albert A, Adv. Heterocycl. Chem. 1986 40 129
3. Bast K, Christl M, Huisgen R, Mack W, Chem. Ber. 1972 105 2825
4. Koguro K, Oga T, Mitsui S, Orita R, Synthesis 1998 910
5. Finnegan W G., Henry R A., Lofquist R, J. Am. Chem. Soc. 1958 80 3908
6. Labbe G, Bruynseels M, Beenaerts L, Vandendriessche A, Delbeke P, Toppet S, Bull. Soc. Chim. Belg. 1989 98 343
7. Smith P A. S., The Organic Chemistry of Open-Chain Nitrogen Compounds Vol. 1 Benjamin New York 1965 Chap. 5 209-231
8. Friedrich K, Wallenfels K, In The Chemistry of Cyano Group Rappoport Z Wiley-Interscience New York 1970 Chap. 2 67-122
9. Harrison I T., Harrison S, In Compendium of Organic Synthetic Methods Vol. 1 Wiley Interscience New York 1971 Chap. 13 457-478
10. Metzger H, In Methoden der Organischen Chemie (Houben-Weyl) Vol. 10, Part 4 Mller E Thieme Stuttgart 1968 217-282
11. Naumov Y A., Grandberg I I., Russ. Chem. Rev. 1966 35 9
12. Starosotnikov A M., Lobach A V., Shevelev S A., Synthesis 2005 2830
13. Mano T, Stevens R W., Ando K, Kawai M, Kawamura K, Nakao K, Okumura Y, Okumura T, Sakakibara M, Miyamoto K, Tamura T, Chem. Pharm. Bull. 2005 53 965
14. Konkel J T., Fan J, Jayachandran B, Kirk K L., J. Fluorine Chem. 2002 115 27
15. Clive D L. J., Wang J, J. Org. Chem. 2004 69 2773
16. Poschalko A, Welzig S, Treu M, Nerdinger S, Mereiter K, Jordis U, Tetrahedron 2002 58 1513
17. Narsaiah A V., Sreenu D, Nagaiah K, Synth. Commun. 2006 36 137
18. Yang S H., Chang S, Org. Lett. 2001 3 4209
19. Narsaiah A V., Nagaiah K, Adv. Synth. Catal. 2004 346 1271
20. Lwe W, Witzel S, Tappmeyer S, Albuschat R, J. Heterocycl. Chem. 2004 41 317
21. Movassagh B, Shokri S, Synth. Commun. 2005 35 887
22. Miller C P., Kaufman D H., Synlett 2000 1169, Lutz A W., Diehl R E., US 4288385 1981; Chem. Abstr. 1981, 96: 103821
23. Beare N A., Hartwig J F., J. Org. Chem. 2002 67 541
24. Stauffer S R., Beare N A., Stambuli J P., Hartwig J F., J. Am. Chem. Soc. 2001 123 4641
25. Kowalczyk B A., Synthesis 1997 1411
26. Padmavathi V, Balaiah A, Reddy B J. M., Padmaja A, Heterocycl. Commun. 2003 9 599