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

Synthesis

Volumn , Issue 18, 2002, Pages 2717-2724

  Resnyanskaya, Elizaveta V ^a   Tverdokhlebov, Anton V ^a   Volovenko, Yulian M ^a   Shishkin, Oleg V ^b   Zubatyuk, Roman I ^b  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b INSTITUTE FOR SINGLE CRYSTALS   (Ukraine)

Author keywords

5 amino 2 pyrrolones; Acylations; Alkylations; Heterocycles; Pyrrolo 2 ,3 :4,5 pyrimido 6,1 b benzothiazoles

Indexed keywords

ACYLATION; ALKYLATION; AROMATIC HYDROCARBONS; X RAY CRYSTALLOGRAPHY;

HETEROCYCLIC SYSTEMS;

SYNTHESIS (CHEMICAL);

1 BENZOYL 3,5 DIPHENYL 3H PYRROLO[2',3':4,5]PYRIMIDO[6,1 B]BENZOTHIAZOL 6 IUM 2 OLATE; 2 BENZOTHIAZOLEACETONITRILE; 3H PYRROLO[2',3':4,5]PYRIMIDO[6,1 B]BENZOTHIAZOL 6 IUM 2 OLATE; 4 (2 BENZOTHIAZOLYL) 2,3 DIHYDRO 2 PYRROLONE; ACETONITRILE DERIVATIVE; ANILIDE; BENZOTHIAZOLE DERIVATIVE; BETAINE DERIVATIVE; CHLORIDE; CHLOROACETIC ACID ANILIDE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0036930420     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35992     Document Type: Article

References (34)

1. (a) Volovenko, Yu. M.; Gofman, L. V.; Babichev, F. S. Dopov. Akad. Nauk Ukr. 1978, 7, 621; Chem. Abstr. 1978, 89, 163331.
2. (b) Volovenko, Yu. M.; Gofman, L. V.; Babichev, F. S. Ukr. Khim. Zh. (Russ. Ed.) 1979, 45, 857; Chem. Abstr. 1980, 92. 22356.
3. (c) Volovenko, Yu. M.; Shokol, T. V.; Babichev, F. S. Ukr. Khim. Zh. (Russ. Ed.) 1985, 51, 205; Chem. Abstr. 1985, 103, 71276.
4. (d) Volovenko, Yu. M.; Shokol, T. V.; Dashkovskaya, E. V.; Babichev, F. S. Ukr. Khim. Zh. (Russ. Ed.) 1985, 51, 649; Chem. Abstr. 1986, 104, 19487.
5. (e) Volovenko, Yu. M.; Shokol, T. V.; Tverdokhlebov, A. V.; Babichev, F. S. Khim. Geterotsikl. Soedin. 1996, 1000; Chem. Abstr. 1996, 124, 125446.
6. (a) Babichev, F. S.; Volovenko, Yu. M. Khim. Geterotsikl. Soedin. 1976, 1147; Chem. Abstr. 1976, 85, 177228.
7. (b) Babichev, F. S.; Volovenko, Yu. M. Ukr. Khim. Zh. (Russ. Ed.) 1977, 43, 711; Chem. Abstr. 1977, 87, 184451.
8. (c) Volovenko, Yu. M.; Babichev, F. S. Khim. Geterotsikl. Soedin. 1977, 557; Chem. Abstr. 1977, 87, 68254.
9. (d) Volovenko, Yu. M.; Shokol, T. V.; Merkulov, A. S.; Babichev, F. S. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59, 55; Chem. Abstr. 1993, 119, 160185.
10. (e) Tverdokhlebov, A. V.; Volovenko, Yu. M.; Shokol, T. V. Chem. Heterocycl. Cmpd. (Engl. Transl.) 1998, 34, 44.
11. (f) Resnyanskaya, E. V.; Shokol, T. V.; Volovenko, T. V.; Tverdokhlebov, A. V. Chem. Heterocycl. Cmpd. (Engl. Transl.) 1999, 35, 1230.
12. (g) Volovenko, Yu. M.; Volovnenko, T. A.; Tverdokhlebov, A. V.; Ryabokon, I. G. Russ. J. Org. Chem. 2001, 37, 1323.
13. (h) Volovenko, Yu. M.; Tverdokhlebov, A. V.; Gorulya, A. P.; Shishkina, S. V.; Zubatyuk, R. I.; Shishkin, O. V. Eur. J. Org. Chem. 2002, 663.
14. Gola, A.; Samartzi, E.; Bardakos, V.; Petroliagi, M.; Igglessi-Markopoulou, O.; Markopoulos, J.; Barkley, J. V. J. Heterocycl. Chem. 2000, 37, 681.
15. (a) Schäfer, H.; Gewald, K. Monatsh. Chem. 1989, 120, 315.
16. (b) Berghot, M. A.; Hanna, M. A.; Girges, M. M. Pharmazie 1992, 47, 340.
17. (c) Ghorab, M. M.; Abdel-Hamide, S. G.; El-Hakim, A. E. Indian J. Heterocycl. Chem. 1995, 5, 115.
18. (d) Abdel-Hamide, S. G. J. Indian Chem. Soc. 1997, 74, 613.
19. (e) Ghorab, M. M.; Nassar, O. M.; Heiba, H. I.; Amin, N. E. Acta Pharm. (Zagreb) 1998, 48, 101; Chem. Abstr. 1998, 129, 239599.
20. (f) Ibrahim, M. K. Egypt. J. Pharm. Sci. 1999, 39, 519; Chem. Abstr. 2000, 133, 237942.
21. (g) Abbady, M. A.; Abdel-Hafez, Sh. H. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 160, 121.
22. Bahner, C. T.; Pickens, D.; Bales, D. B. J. Am. Chem. Soc. 1948, 70, 1652.
23. Nakanishi, K. Infra Red Absorbtion Spectroscopy; Holden-Day: San Francisco, 1962.
24. (a) Gakhar, H. K.; Chand, S. Monatsh. Chem. 1981, 112, 1083.
25. (b) Molina, P.; Alajarin, M.; Vidal, A.; Foces-Foces, M.; Hernandez, C. F. Tetrahedron 1989, 45, 4263.
26. (a) Winter, W.; Roesch, E.; Wilhelms, O. H.; Roesch, A.; Hindermayr, H. S. African Pat. Appl. ZA 79-1053, 1980.
27. (b) Winter, W.; Hindermayr, H.; Roesch, A.; Roesch, E.; Wilhelms, O. H. Ger. Often. DE 2810863, 1979; Chem. Abstr. 1979, 92, 41982.
28. (c) Ley, K.; Aichinger, G.; Botta, A.; Hagemann, H.; Niemers, E. Ger. Often. DE 2126148, 1972; Chem. Abstr. 1972, 78, 111360.
29. (a) Fathy, N. M.; Elgemeie, G. E. H. Sulfur Lett. 1988, 7, 189.
30. (b) Elgemeie, G. E. H.; Abd El Aal, F. A. M. Heterocycles 1986, 24, 349.
31. Zefirov, Yu. V.; Zorky, P. M. Russ. Chem. Rev. 1989, 58, 421.
32. Saito, K.; Kambe, S.; Nakano, Y. Synthesis 1983, 210.
33. Balls, A. K.; Kohler, F. Ber. Dtsch. Chem. Ges. 1931, 64, 34.
34. Sheldrick, G. M. SHLEX97. PC Version. A System of Computer Programs for Coastal Structure Solution and Refinement, Rev. 2; University of Göttingen: Germany, 1998.