Download PDF
Synthesis 2002(18): 2717-2724
DOI: 10.1055/s-2002-35992
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Simple Synthesis of 1-Acyl-3-aryl-3H-pyrrolo[2′,3′:4,5]pyrimido[6,1-b]benzothiazol-6-ium-2-olates: Betainic Derivatives of a Novel Heterocyclic System

Elizaveta V. Resnyanskayaa, Anton V. Tverdokhlebov*a, Yulian M. Volovenkoa, Oleg V. Shishkinb, Roman I. Zubatyukb
a Kiev National Taras Shevchenko University, Volodimirska str., 62, 01033, Kiev, Ukraine
e-Mail: atver@mail.univ.kiev.ua;
b Scientific Research Department of Alkali Halide Crystals, STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, 60 Lenina ave., 310001, Khar’kov, Ukraine
Further Information

Publication History

Received 10 July 2002
Publication Date:
06 December 2002 (online)

    Permissions and Reprints All articles of this category

Abstract

The title compounds were obtained by acylation of 5-amino-1-aryl-4-(2-benzothiazolyl)-2,3-dihydro-2-pyrrolones with 3-fold excess of acid chlorides. Starting pyrrolones were prepared in high yields by alkylation of 2-benzothiazoleacetonitrile with chloroacetic acid anilides. An X-ray crystallographic study of 1-benzoyl-3,5-diphenyl-3H-pyrrolo[2′,3′:4,5]pyrimido[6,1-b]benzo­thiazole-6-ium-2-olate was carried out to confirm the structure of title compounds unambiguously. The charge distribution in the obtained betaines was discussed.

Key words

acylations - alkylations - 5-amino-2-pyrrolones - heterocycles - pyrrolo[2′,3′:4,5]pyrimido[6,1-b]benzothiazoles

    References

  • 1a Volovenko YuM. Gofman LV. Babichev FS. Dopov. Akad. Nauk Ukr.   1978,  7:  621 ; Chem. Abstr. 1978 , 89, 163331
    Google Scholar
  • 1b Volovenko YuM. Gofman LV. Babichev FS. Ukr. Khim. Zh. (Russ. Ed.)  1979,  45:  857 ; Chem. Abstr. 1980 , 92, 22356
    Google Scholar
  • 1c Volovenko YuM. Shokol TV. Babichev FS. Ukr. Khim. Zh. (Russ. Ed.)  1985,  51:  205 ; Chem. Abstr. 1985 , 103, 71276
    Google Scholar
  • 1d Volovenko YuM. Shokol TV. Dashkovskaya EV. Babichev FS. Ukr. Khim. Zh. (Russ. Ed.)  1985,  51:  649 ; Chem. Abstr. 1986, 104, 19487
    Google Scholar
  • 1e Volovenko YuM. Shokol TV. Tverdokhlebov AV. Babichev FS. Khim. Geterotsikl. Soedin.  1996,  1000 ; Chem. Abstr. 1996, 124, 125446
    Google Scholar
  • 2a Babichev FS. Volovenko YuM. Khim. Geterotsikl. Soedin.  1976,  1147 ; Chem. Abstr. 1976, 85, 177228
    CrossrefGoogle Scholar
  • 2b Babichev FS. Volovenko YuM. Ukr. Khim. Zh. (Russ. Ed.)  1977,  43:  711 ; Chem. Abstr. 1977, 87, 184451
    CrossrefGoogle Scholar
  • 2c Volovenko YuM. Babichev FS. Khim. Geterotsikl. Soedin.  1977,  557 ; Chem. Abstr. 1977, 87, 68254
    CrossrefGoogle Scholar
  • 2d Volovenko YuM. Shokol TV. Merkulov AS. Babichev FS. Ukr. Khim. Zh. (Russ. Ed.)  1993,  59:  55 ; Chem. Abstr. 1993, 119, 160185
    CrossrefGoogle Scholar
  • 2e Tverdokhlebov AV. Volovenko YuM. Shokol TV. Chem. Heterocycl. Cmpd. (Engl. Transl.)  1998,  34:  44 
    CrossrefGoogle Scholar
  • 2f Resnyanskaya EV. Shokol TV. Volovenko TV. Tverdokhlebov AV. Chem. Heterocycl. Cmpd. (Engl. Transl.)  1999,  35:  1230 
    CrossrefGoogle Scholar
  • 2g Volovenko YuM. Volovnenko TA. Tverdokhlebov AV. Ryabokon IG. Russ. J. Org. Chem.  2001,  37:  1323 
    CrossrefGoogle Scholar
  • 2h Volovenko YuM. Tverdokhlebov AV. Gorulya AP. Shishkina SV. Zubatyuk RI. Shishkin OV. Eur. J. Org. Chem.  2002,  663 
    CrossrefGoogle Scholar
  • 3 Gola A. Samartzi E. Bardakos V. Petroliagi M. Igglessi-Markopoulou O. Markopoulos J. Barkley JV. J. Heterocycl. Chem.  2000,  37:  681 
    Google Scholar
  • 4a Schäfer H. Gewald K. Monatsh. Chem.  1989,  120:  315 
    Google Scholar
  • 4b Berghot MA. Hanna MA. Girges MM. Pharmazie  1992,  47:  340 
    Google Scholar
  • 4c Ghorab MM. Abdel-Hamide SG. El-Hakim AE. Indian J. Heterocycl. Chem.  1995,  5:  115 
    Google Scholar
  • 4d Abdel-Hamide SG. J. Indian Chem. Soc.  1997,  74:  613 
    Google Scholar
  • 4e Ghorab MM. Nassar OM. Heiba HI. Amin NE. Acta Pharm. (Zagreb)  1998,  48:  101 ; Chem. Abstr. 1998, 129, 239599
    Google Scholar
  • 4f Ibrahim MK. Egypt. J. Pharm. Sci.  1999,  39:  519 ; Chem. Abstr. 2000, 133, 237942
    Google Scholar
  • 4g Abbady MA. Abdel-Hafez ShH. Phosphorus, Sulfur Silicon Relat. Elem.  2000,  160:  121 
    Google Scholar
  • 5 Bahner CT. Pickens D. Bales DB. J. Am. Chem. Soc.  1948,  70:  1652 
    Google Scholar
  • 6 Nakanishi K. Infra Red Absorbtion Spectroscopy   Holden-Day; San Francisco: 1962. 
    Google Scholar
  • 7a Gakhar HK. Chand S. Monatsh. Chem.  1981,  112:  1083 
    CrossrefGoogle Scholar
  • 7b Molina P. Alajarin M. Vidal A. Foces-Foces M. Hernandez CF. Tetrahedron  1989,  45:  4263 
    CrossrefGoogle Scholar
  • 8a Winter W, Roesch E, Wilhelms OH, Roesch A, and Hindermayr HS. inventors; African Pat. Appl. ZA  79-1053. 
  • 8b Winter W, Hindermayr H, Roesch A, Roesch E, and Wilhelms OH. inventors; Ger. Offen. DE  2810863.  ; Chem. Abstr. 1979, 92, 41982
  • 8c Ley K, Aichinger G, Botta A, Hagemann H, and Niemers E. inventors; Ger. Offen. DE  2126148.  ; Chem. Abstr. 1972, 78, 111360
  • 9a Fathy NM. Elgemeie GEH. Sulfur Lett.  1988,  7:  189 
    Google Scholar
  • 9b Elgemeie GEH. Abd El Aal FAM. Heterocycles  1986,  24:  349 
    Google Scholar
  • 10 Zefirov YuV. Zorky PM. Russ. Chem. Rev.  1989,  58:  421 
    Google Scholar
  • 11 Saito K. Kambe S. Nakano Y. Synthesis  1983,  210 
    Article in Thieme ConnectGoogle Scholar
  • 12 Balls AK. Kohler F. Ber. Dtsch. Chem. Ges.  1931,  64:  34 
    CrossrefGoogle Scholar
  • 13 Sheldrick GM. SHLEX97. PC version. A System of Computer Programs for Crystal Structure Solution and Refinement   Rev. 2:  University of Göttingen; Germany: 1998. 
    Google Scholar