Skip to main content
SpringerLink
Log in

Synthesis of Pyrrolo[2,1-b]thiazol-3-one Derivatives

  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

Ethyl [4-oxo-3-(2-oxo-2-arylethyl)thiazolidin-2-ylidene]acetates and [4-oxo-3-(2-oxo-2-arylethyl)thiazolidin-2-ylidene]acetonitriles were shown to react with substituted benzaldehydes at the endocyclic methylene group leading to the corresponding 5-arylmethylidene derivatives. Their treatment with DMF · POCl3 complex yielded 3-oxo-5-aroyl-2-arylmethylidene-2,3-dihydropyrrolo[2,1-b]thiazole-7-carboxylic acids ethyl esters and -7-carbonitriles. The structures of the pyrrolothiazoles were confirmed by an X-ray crystallographic study, which indicated the (Z)-configuration at the arylmethylidene moiety.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Wasserman HH, Suryanarayana B, Koch RC, Tse RL (1956) Chem Ind (London) 1022

  • HH Wasserman FM Precopio TC Liu (1952) J Am Chem Soc 74 4093 Occurrence Handle10.1021/ja01136a038

    Article  Google Scholar 

  • JE Baldwin MF Chan G Gallacher M Otsuka (1984) Tetrahedron 40 4513 Occurrence Handle10.1016/S0040-4020(01)98828-3

    Article  Google Scholar 

  • Baldwin JE, Chan MF, Gallacher G, Monk P, Prout K (1983) J Chem Soc Chem Commun 250

  • Maki Y, Sako M, Kurahashi N, Hirota K (1988) J Chem Soc Chem Commun 110

  • EM Gordon J Pluscec (1983) Tetrahedron Lett 24 3419 Occurrence Handle10.1016/S0040-4039(00)86002-5

    Article  Google Scholar 

  • HW Moore MJ Arnold (1983) J Org Chem 48 3365 Occurrence Handle10.1021/jo00167a056

    Article  Google Scholar 

  • GL Oliver JR Dann JW Gates (1958) J Am Chem Soc 80 702 Occurrence Handle10.1021/ja01536a045

    Article  Google Scholar 

  • IT Strukow (1952) Zh Obshch Khim 22 521

    Google Scholar 

  • RJ Hiskey SJ Dominianni (1965) J Org Chem 30 1506

    Google Scholar 

  • Hellstrom N, Almqvist SO, Aamisepp M, Rodmar S (1968) J Chem Soc (C) 392

  • JE Baldwin MA Christie (1978) J Am Chem Soc 100 4597 Occurrence Handle10.1021/ja00482a048

    Article  Google Scholar 

  • JE Baldwin E Lee (1986) Tetrahedron 42 6551 Occurrence Handle10.1016/S0040-4020(01)88118-7

    Article  Google Scholar 

  • JE Baldwin RT Freeman C Lowe CJ Schofield E Lee (1989) Tetrahedron 45 4537 Occurrence Handle10.1016/S0040-4020(01)89088-8

    Article  Google Scholar 

  • JE Baldwin C Lowe CJ Schofield (1986) Tetrahedron Lett 27 3461 Occurrence Handle10.1016/S0040-4039(00)84822-4

    Article  Google Scholar 

  • H Schafer K Gewald (1974) J Prakt Chem 316 684 Occurrence Handle10.1002/prac.19743160421

    Article  Google Scholar 

  • A Dondoni G Fatin M Fogagnolo A Medici (1984) Heterocycles 22 2341

    Google Scholar 

  • Gupta AK, Ila H, Junjappa H (1988) Synthesis 284

  • NE Allen DB Boyd JB Campbell JB Deeter TK Elzey BJ Foster LD Hatfield JN Hobbs WJ Hornback DC Hunden ND Jones MD Kinnick JM Morin JE Munroe JK Swartzendruber DC Vogt (1989) Tetrahedron 45 1905 Occurrence Handle10.1016/S0040-4020(01)80055-7

    Article  Google Scholar 

  • DB Boyd TK Elzey LD Hatfield MD Kinnick JM Morin (1986) Tetrahedron Lett 27 3453 Occurrence Handle10.1016/S0040-4039(00)84820-0

    Article  Google Scholar 

  • EM Khalil A Pradhan WH Ojala WB Cleason RK Mishra RL Johnson (1999) J Med Chem 42 2977 Occurrence Handle10.1021/jm990140n Occurrence Handle10425107

    Article  PubMed  Google Scholar 

  • NL Subasinghe RJ Bontems E McIntee RK Mishra RL Johnson (1993) J Med Chem 36 2356 Occurrence Handle10.1021/jm00068a013 Occurrence Handle8103113

    Article  PubMed  Google Scholar 

  • TD Aicher B Balkan PA Bell LJ Brand SH Cheon RO Deems JB Fell WS Fillers JD Fraser J Gao DC Knorr GG Kahle CL Leone J Nadelson R Simpson HC Smith (1998) J Med Chem 41 4556 Occurrence Handle10.1021/jm9803121 Occurrence Handle9804695

    Article  PubMed  Google Scholar 

  • T Burgemeister G Dannhardt E Graf R Obergrusberger (1987) Arch Pharm 320 799

    Google Scholar 

  • G Dannhardt T Debaerdemaeker (1987) Arch Pharm 320 1278

    Google Scholar 

  • DE Butler JD Leonard BW Caprathe YJ L’Italien MR Pavia FM Hershenson PH Poschel JG Marriott (1987) J Med Chem 30 498 Occurrence Handle10.1021/jm00386a010 Occurrence Handle3820221

    Article  PubMed  Google Scholar 

  • Bespalova GV, Sedavkina VA, Ponomareva EV, Shebaldova AD, Labunskaya VI (1986) Khim Geterotsikl Soedin 1690; Chem Heterocycl Compd (Engl Transl) 22: 1370 (1986)

    Google Scholar 

  • A Padwa ZJ Zhang (1994) Heterocycles 37 441

    Google Scholar 

  • A Padwa LS Beall TM Heidelbaugh B Liu SM Sheehan (2000) J Org Chem 65 2684 Occurrence Handle10.1021/jo991742h Occurrence Handle10808441

    Article  PubMed  Google Scholar 

  • Y Terao Y Yasumoto K Ikeda M Sekiya (1986) Chem Pharm Bull 34 105

    Google Scholar 

  • AK El-Shafei AM El-Sayed H Abdel-Ghany AM El-Saghier (1990) Gazz Chim Ital 120 193

    Google Scholar 

  • GWH Cheeseman AA Hawi (1983) J Heterocycl Chem 20 591

    Google Scholar 

  • Coulton S, Southgate R (1992) J Chem Soc Perkin Trans 1, 961

  • Tverdokhlebov AV, Resnyanska EV, Tolmachev AA, Andrushko AP (2003) Synthesis 2632

  • Tverdokhlebov AV, Andrushko AP, Resnyanska EV, Tolmachev AA (2004) Synthesis 2317

  • MH Elnagdi RMH Elmoghayar AEFG Hamman SA Khallaf (1979) J Heterocycl Chem 16 1541

    Google Scholar 

  • Satzinger G (1963) Liebigs Ann Chem 151

  • JL Isidor RL McKee (1973) J Org Chem 38 3615

    Google Scholar 

  • Satzinger G (1978) Liebigs Ann Chem 473

  • Kambe S, Saito K, Kishi H, Hayashi T, Sakurai A (1977) Synthesis 839

  • Kambe S, Saito K, Sakurai A, Midorikawa H (1980) Synthesis 839

  • SM Sherif (1996) Monatsh Chem 127 557 Occurrence Handle10.1007/BF00807035

    Article  Google Scholar 

  • NS Habib SM Rida EAM Badawey HTY Fahmy HA Ghozlan (1997) Pharmazie 52 346 Occurrence Handle9183785

    PubMed  Google Scholar 

  • TS Jagodzinski A Wesolowska JG Sosniski (2001) Pol J Chem 140 422

    Google Scholar 

  • Sheldric GM (1997) SHELXS97. Program for the Solution of Crystal Structures. University of Göttingen, Germany

  • Sheldric GM (1997) SHELXL97. Program for the Refinement of Crystal Structures. University of Göttingen, Germany

Download references

Author information

Authors and Affiliations

  1. Enamine Ltd., 01103, Kiev, Ukraine

    Anton V. Tverdokhlebov & Alexander P. Andrushko

  2. Kiev National Taras Shevchenko University, 01033, Kiev, Ukraine

    Andrey A. Tolmachev

  3. Institute of Organic Chemistry NAS, 02094, Kiev, Ukraine

    Alexander N. Kostyuk, Alexander N. Chernega & Eduard B. Rusanov

Authors
  1. Anton V. Tverdokhlebov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alexander P. Andrushko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Andrey A. Tolmachev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alexander N. Kostyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Alexander N. Chernega
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Eduard B. Rusanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anton V. Tverdokhlebov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tverdokhlebov, A., Andrushko, A., Tolmachev, A. et al. Synthesis of Pyrrolo[2,1-b]thiazol-3-one Derivatives. Monatsh. Chem. 136, 1781–1790 (2005). https://doi.org/10.1007/s00706-005-0356-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-005-0356-1

Search

Navigation