Parallel Synthesis of a Library of Acylsemicarbazides Using a Solution-Phase One-Pot Method and Their Evaluation as Crop-Protection Agents

Justyna A. Grzyb; Mark A. Dekeyser; Robert A. Batey

doi:10.1055/s-2005-870020

PAPER

Parallel Synthesis of a Library of Acylsemicarbazides Using a Solution-Phase One-Pot Method and Their Evaluation as Crop-Protection Agents

Justyna A. Grzyb^a, Mark A. Dekeyser^b, Robert A. Batey*^a
^a Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada
Fax: +1(416)9785059; e-Mail: rbatey@chem.utoronto.ca;
^b Crompton Co. Research Laboratories, Box 1120, Guelph, Ontario, N1H 6N3, Canada

Abstract

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Abstract

A solution-phase one-pot synthesis of a 40-member acylsemicarbazide library is outlined. The acylsemicarbazides were prepared by reacting various hydrazides with N,N′-carbonyldiimidazole (CDI) to generate 1,3,4-oxadiazole-2-one intermediates, which were then opened in situ with amines. Purification in the majority of cases was accomplished through filtration of the precipitated product in generally good yields and with ³ 95% purities. An analogous synthesis of acylthiosemicarbazides was accomplished using N,N′-thiocarbonyldiimidazole (TCDI). The library was then assayed for herbicidal, insecticidal, fungicidal and plant growth regulatory behavior.

Key words

acylsemicarbazides - acylthiosemicarbazides - 1,3,4-oxadiazol-2-one - solution phase - library - crop protection

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Referenzen

References

1a Gante J. Synthesis 1989, 405

1b Gibson C. Goodman SL. Hahn D. Hölzemann G. Kessler H. J. Org. Chem. 1999, 64: 7388

1c Weber D. Berger C. Eickelmann P. Antel J. Kessler H. J. Med. Chem. 2003, 46: 1918

2 Andurkar SV. Béguin C. Stables JP. Kohn H. J. Med. Chem. 2001, 44: 1475

3a Wing KD. Science 1988, 241: 467

3b Wing KD. Slawecki RA. Carlson GR. Science 1988, 241: 470

4a Nakagawa Y. Smagghe G. Kugimiya S. Hattori K. Ueno T. Tirry L. Fujita T. Pestic. Sci. 1999, 55: 909

4b Mulvihill MJ. Shaber SH. MacDougall BS. Ajello C. Martinez-Teipel B. Joseph R. Nguyen DV. Weaver DG. Chung K.-H. Gusev A. Wierenga JM. Mathis WD. Synthesis 2002, 53

5 Wang Q. Huang R. Tetrahedron Lett. 2001, 42: 8881

For reviews on solid-phase organic synthesis, see:

6a Krchnák V. Holladay MW. Chem. Rev. 2002, 102: 61

6b Lorsbach BA. Kurth MJ. Chem. Rev. 1999, 99: 1549

6c Kobayashi S. Chem. Soc. Rev. 1999, 28: 1

6d Brown AR. Hermkens PHH. Ottenheijm HCJ. Rees DC. Synlett 1998, 817

6e Brown RCD. J. Chem. Soc., Perkin Trans. 1 1998, 3293

6f Nefzi A. Ostresh JM. Houghten RA. Chem. Rev. 1997, 97: 449

6g Thompson LA. Ellman JA. Chem. Rev. 1996, 96: 555

For reviews on liquid-phase organic synthesis, see:

7a Sun C.-M. Comb. Chem. High Throughput Screening 1999, 2: 299

7b Wentworth P. Trends Biotechnol. 1999, 17: 448

7c Wentworth P. Janda KD. Chem. Commun. 1999, 1917

7d Gravert DJ. Janda KD. Chem. Rev. 1997, 97: 489

For reviews on solution-phase organic synthesis, see:

8a An H. Cook PD. Chem. Rev. 2000, 100: 3311

8b Merritt AT. Comb. Chem. High Throughput Screening 1998, 1: 57

8c Boger DL. Goldberg J. J. Comb. Chem. 2000, 303

8d Coe DM. Storer R. Mol. Diversity 1999, 4: 31

9a Peng SX. Henson C. Strojnowski MJ. Golebiowski A. Klopfenstein SR. Anal. Chem. 2000, 72: 261

9b Chen Y. Bilban M. Foster CA. Boger DL. J. Am. Chem. Soc. 2002, 124: 5431

10a Curran DP. Angew. Chem. Int. Ed. Engl. 1998, 37: 1174

10b Curran DP. Hadida S. J. Am. Chem. Soc. 1996, 118: 2531

10c Curran DP. Hoshino M. J. Org. Chem. 1996, 61: 6480

10d Studer A. Curran DP. Tetrahedron 1997, 53: 6681

10e Studer A. Jeger P. Wipf P. Curran DP. J. Org. Chem. 1997, 62: 2917

10f Curran DP. Hadida S. He M. J. Org. Chem. 1997, 62: 6714

11a Parlow JJ. Devraj RV. South MS. Curr. Opin. Chem. Biol. 1999, 3: 320

11b Song CE. Le S.-G. Chem. Rev. 2002, 102: 3495

11c Ley SV. Baxendale IR. Brusotti G. Caldarelli M. Massi A. Nesi M. Il Farmaco 2002, 57: 321

11d Ley SV. Baxendale IR. Bream RN. Jackson PS. Leach AG. Longbottom DA. Nesi M. Scott JS. Storer RI. Taylor SJ. J. Chem. Soc., Perkin Trans. 1 2000, 3815

11e Booth RJ. Hodges JC. Acc. Chem. Res. 1999, 32: 18

11f Weller HN. Mol. Diversity 1999, 4: 47

12a Shuttleworth SJ. Quimpére M. Lee N. DeLuca J. Mol. Diversity 1998, 4: 183

12b Kang KH. Pae AN. Choi KI. Cho YS. Chung BY. Lee JE. Jung SH. Koh HY. Lee H.-Y. Tetrahedron Lett. 2001, 42: 1057

12c Tietze LF. Evers H. Töpken E. Helv. Chim. Acta 2002, 85: 4200

12d Tietze LF. Evers H. Töpken E. Angew. Chem. Int. Ed. 2001, 40: 903

12e Beaulieu PL. Haché B. von Moos E. Synthesis 2003, 1683

12f Lee H.-K. Chui W.-K. Bioorg. Med. Chem. 1999, 7: 1255

12g Pirrung MC. Sarma KD. J. Am. Chem. Soc. 2004, 126: 444

13a Honigfort ME. Brittain WJ. Bosanac T. Wilcox CS. Macromolecules 2002, 35: 4849

13b Bosanac T. Wilcox CS. J. Am. Chem. Soc. 2002, 124: 4194

13c Bosanac T. Yang J. Wilcox CS. Angew. Chem. Int. Ed. 2001, 40: 1875

14a Ahn J.-M. Wentworth P. Janda KD. Chem. Commun. 2003, 480

14b Sieber F. Wentworth P. Janda KD. J. Comb. Chem. 1999, 1: 540

14c Zhao X.-Y. Metz WA. Sieber F. Janda KD. Tetrahedron Lett. 1998, 39: 8433

14d Huang K.-T. Sun C.-M. Bioorg. Med. Chem. Lett. 2002, 12: 1001

14e Huang K.-T. Sun C.-M. Bioorg. Med. Chem. Lett. 2001, 11: 271

14f Sun C.-M. Shey J.-Y. J. Comb. Chem. 1999, 1: 361

14g Shey J.-Y. Sun C.-M. Bioorg. Med. Chem. Lett. 1999, 9: 519

14h Ho K.-C. Sun C.-M. Bioorg. Med. Chem. Lett. 1999, 9: 1517

15a Davidson JS. Monatsh. Chem. 1988, 119: 1027

15b Novikov MS. Khlebnikov AF. Stepanov AA. Kostikov RR. Synthesis 1994, 782

16a Stillings MR. Freeman S. Myers PL. Readhead MJ. Welbourn AP. Rance MJ. Atkinson DC. J. Med. Chem. 1985, 28: 225

16b Yale HL. Losee KA. Perry FM. Bernstein J. J. Am. Chem. Soc. 1954, 76: 2208

17a Batey RA. Santhakumar V. Yoshina-Ishii C. Taylor SD. Tetrahedron Lett. 1998, 39: 6267

17b Batey RA. Yoshina-Ishii C. Taylor SD. Santhakumar VA. Tetrahedron Lett. 1999, 40: 2669

17c Grzyb JA. Batey RA. Tetrahedron Lett. 2003, 44: 7485

For examples of the use of CDI in parallel synthesis, see:

18a Acharya AN. Ostresh JM. Houghten RA. Tetrahedron 2002, 58: 2095

18b Nefzi A. Giulianotti M. Truong L. Rattan S. Ostresh JM. Houghten RA. J. Comb. Chem. 2002, 4: 175

18c Nefzi A. Ostresh JM. Giulianotti M. Houghten RA. J. Comb. Chem. 1999, 1: 195

18d Deegan TL. Nitz TJ. Cebzanov D. Pufko DE. Porco JA. Bioorg. Med. Chem. Lett. 1999, 9: 6267

18e Nefzi A. Ostresh JM. Meyer J.-P. Houghten RA. Tetrahedron Lett. 1997, 38: 931

19a Firoozi F. Javidnia K. Kamali M. Fooladi A. Foroumadi A. Shafiee A. J. Heterocycl. Chem. 1995, 32: 123

19b Mullican MD. Wilson MW. Connor DT. Kostlan CR. Schrier DJ. Dyer RD. J. Med. Chem. 1993, 36: 1090

19c Davidson JS. Monatsh. Chem. 1984, 115: 565

19d Tihanyi E. Gál M. Dvortsák P. Heterocycles 1983, 20: 571

20a Stempel A. Zelauskas J. Aeschlimann JA. J. Org. Chem. 1955, 20: 412

20b Saegusa Y. Harada S. Nakamura S. J. Heterocycl. Chem. 1988, 25: 1337

21 Chau N. Saegusa Y. Iwakura Y. J. Heterocycl. Chem. 1982, 19: 541

22 Kramer JB. Boschelli DH. Connor DT. J. Heterocycl. Chem. 1994, 31: 1439

23 Pancechowska-Ksepko D. Foks H. Janowiec M. Zwolska-Kwiek Z. Acta Pol. Pharm. 1993, 50: 259

Other nucleophiles that are known to ring-open 1,3,4-oxadiazole-2-ones via nucleophilic attack include hydrazines and thiols, for example, see ref. 20 and:

24a Thompson SK. Halbert SM. DesJarlais RL. Tomaszek TA. Levy MA. Tew DG. Ijames CF. Veber DF. Bioorg. Med. Chem. 1999, 7: 599

24b Kristinsson H. Winkler T. Mollenkopf M. Helv. Chim. Acta 1986, 69: 333

24c Werbel LM. McNamara DJ. Colbry NL. Johnson JL. Degnan MJ. Whitney B. J. Heterocycl. Chem. 1979, 16: 881