Imidazo[1,2]hetarylglyoxylates: Synthesis and reactivity toward nucleophiles

Synthesis

Volumn , Issue 10, 2010, Pages 1692-1696

  Zamkova, Irina A ^a   Chekotylo, Oleksiy O ^a   Geraschenko, Oleksandr V ^a,b   Grygorenko, Oleksandr O ^a,b   Mykhailiuk, Pavel K ^a,b   Tolmachev, Andrey A ^a,b  

^a ENAMINE LTD   (Ukraine)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

Author keywords

Acylation; Glyoxylates; Imidazoheterocycles; Privileged scaffolds

Indexed keywords

DRUG DISCOVERY; ELECTRON DONATING PROPERTIES; FRIEDEL-CRAFTS ACYLATION; GLYOXYLATES; HETEROCYCLES; KETO ESTER; OXALYL CHLORIDE;

ACYLATION; CHLORINE COMPOUNDS; DRUG PRODUCTS; ESTERS; NUCLEOPHILES; SYNTHESIS (CHEMICAL);

SCAFFOLDS;

ALPHA KETO ESTER DERIVATIVE; ESTER DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZO[1,2]HETARYLGLYOXYLIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; MOLECULAR SCAFFOLD; NUCLEOPHILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG RESEARCH; ELECTRON TRANSPORT; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 77952042082     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218739     Document Type: Article

References (26)

1. Evans B E., Rittle K E., Bock M G., DiPardo R M., Freidinger R M., Whitter W L., Lundell G F., Veber D F., Anderson P S., Chang R S. L., Lotti V J., Cerino D J., Chen T B., Kling P J., Kunkel K A., Springer J P., Hirshfield J, J. Med. Chem. 1988 31 2235
2. Duarte C D., Barreiro E J., Fraga C A., Mini-Rev. Med. Chem. 2007 7 1108
3. DeSimone R W., Currie K S., Mitchell S A., Darrow J W., Pippin D A., Comb. Chem. High Throughput Screening 2004 7 473
4. Costantino L, Barlocco D, Curr. Med. Chem. 2006 13 65
5. Langer S Z., Arbilla S, Benavides J, Scatton B, Adv. Biochem. Psychopharmacol. 1990 46 61
6. George P, Rossey G, Depoortere H, Mompon B, Allen J, Wick A, Farmaco 1991 46 277
7. Mizushige K, Ueda T, Yukiiri K, Suzuki H, Cardiovasc. Drug. Rev. 2002 20 163
8. Carminati G M., Farmaco Prat. 1978 33 68
9. For selected examples, see:, Primofiore G, DaSettimo F, Taliani S, Marini A M., LaMotta C, Novellino E, Greco G, Gesi M, Trincavelli L, Martini C, J. Med. Chem. 2000 43 96
10. Tse B, Jones A B., Tetrahedron Lett. 2001 42 6429
11. Zhu G, Conner S, Zhou X, Shih C, Brooks H B., Considine E, Dempsey J A., Ogg C, Patel B, Schultz R M., Spencer C D., Teicher B, Watkins S A., Bioorg. Med. Chem. Lett. 2003 13 1231
12. Willardsen J A., Dudley D A., Cody W L., Chi L, McClanahan T B., Mertz T E., Potoczak R E., Narasimhan L S., Holland D R., Rapundalo S T., Edmunds J J., J. Med. Chem. 2004 47 4089
13. Kishorebabu N, Periasamy M, Tetrahedron Lett. 2006 47 2107
14. Clayton J R., Diefenbacher C G., Engler T A., Furness K W., Henry J R., Malhotra S, Marquart A L., McLean J A., Mendel D, Burkholder T P., Li Y, Reel J K., WO03076442 2003; Chem. Abstr. 2003, 139, 261331
15. Recently, the Friedel-Crafts acylation of benzene derivatives with ethyl oxalyl chloride was applied to the synthesis of ethyl arylglyoxylates, see:, Xiang J M., Li B L., Chin. Chem. Lett. 2009 20 55
16. Anisimova V A., Simonov A M., Chem. Heterocycl. Compd. 1976 12 110
17. Anisimova V A., Korochina T B., Avdyunina N I., Simonov A M., Chem. Heterocycl. Compd. 1986 22 275
18. Anisimova V A., Avdyunina N I., Simonov A M., Kovalev G V., Gofman S M., Chem. Heterocycl. Compd. 1976 12 1365
19. Kawamoto T, Tomimatsu K, Ikemoto T, Abe H, Hamamura K, Takatani M, Tetrahedron Lett. 2000 41 3447
20. Daly M, Hopkinson C, J. Chem. Soc., Perkin Trans. 1 1991 855
21. Montgomery J A., Sechrist J A., In Comprehensive Heterocyclic Chemistry Vol. 5 Katritzky A R. Rees C W. Pergamon Press Oxford 1984 608-668
22. Anisimova V A., Avdyunina N I., Pozharskii A F., Simonov A M., Talanova L N., Chem. Heterocycl. Compd. 1980 16 409
23. Tschitschibabin A E., Chem. Ber. 1926 59 2048
24. Djerassi C, Pettit G R., J. Am. Chem. Soc. 1954 76 4470
25. Meakins G D., Musk S R. R., Robertson C A., Woodhouse L S., J. Chem. Soc., Perkin Trans. 1 1989 643
26. Palagiano F, Arenare L, Luraschi E, deCaprariis P, Abignente E, DAmico M, Filippelli W, Rossi F, Eur. J. Med. Chem. 1995 30 901