Synthesis of Unsymmetrical Pyrrolo[3,2-b]pyrrole-2,5-diones

Synlett

Volumn , Issue 15, 2003, Pages 2389-2391

  Langer, Peter ^a   Helmholz, Falko ^a   Schroeder, Rita ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Dilactams of pulvinic acid; One pot synthesis; Unsymmetrical pyrrolo 3,2 b pyrrole 2,5 diones

Indexed keywords

2,2' BISQUINAZOLIN 4 ONE DERIVATIVE; DIMETHYL SULFOXIDE; LACTAM; N,N DIMETHYLFORMAMIDE; OXALIC ACID; PIGMENT; PULVINIC ACID; PYRROLE DERIVATIVE; PYRROLO[3,2 B]PYRROLE 2,5 DIONE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLIZATION; CYCLIZATION; REACTION TIME; STOICHIOMETRY; SYNTHESIS;

EID: 0346749660     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42095     Document Type: Article

References (28)

1. (a) Closs, F.; Gompper, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 552; Angew. Chem. 1987, 99, 564.
2. (a) Closs, F.; Gompper, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 552; Angew. Chem. 1987, 99, 564.
3. (b) Closs, F.; Gompper, R.; Nöth, H.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1988, 27, 842; Angew. Chem. 1988, 100, 875.
4. (b) Closs, F.; Gompper, R.; Nöth, H.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1988, 27, 842; Angew. Chem. 1988, 100, 875.
5. (c) Casser, L.; Iqbal, A.; Rochat, A. C. Eur. Pat. Appl., EP 98808, 1983; Ciba-Geigy.
6. (a) Beyerlein, T.; Tieke, B. Macromol. Rapid Commun. 2000, 21, 182.
7. ( b) Beyerlein, T.; Tieke, B.; Forero-Lenger, S.; Brütting, W. Synth. Metals 2002, 130, 115.
8. (a) Rao, Y. S. Chem. Rev. 1976, 76, 625.
9. (b) Pattenden, G. Prog. Chem. Nat. Prod. 1978, 35, 133.
10. (c) Knight, D. W. Contemp. Org. Synth. 1994, 1, 287.
11. (d) Schweppe, M. Handbuch der Naturfarbstoffe; ecomed Verlagsgesellschaft: Landsberg, 1992, 185.
12. (e) Schweppe, M. Handbuch der Naturfarbstoffe; ecomed Verlagsgesellschaft: Landsberg, 1992, 525.
13. Herbst, W.; Hunger, K. Industrial Organic Pigments; VCH: Weinheim, 1993, 550.
14. Selected symmetrical pyrrolo[3,2-b]pyrrole-2,5-diones have been prepared in three steps from (N-phenylacetyl)-acetic acid amino ester: (a) Bayer AG, a one step synthesis using pulvinic acid proceeded under harsh conditions (autoclave reaction, 140-180°C: Fürstenwerth, H. Ger. Offen., DE 3,525,109 A1, 1987; Chem. Abstr. 1987, 106, 103815f. (b) Ciba-Geigy: Rochat, A. C.; Iqbal, A.; Pfenninger, J.; Casser, L. Eur. Pat. Appl., EP 016309, 1984. See also: Solberg, Y. Z. Naturforsch. 1977, 32c, 292. Stachel, H.-D. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1962, 295, 735. (e) Mukai, T.; Konno, A.; Kumagai, T.; Satake, K. Chem. Lett. 1985, 1809. (f) Stachel, H.-D.; Schorp, M.; Maier, L.; Dandl, K. Liebigs Ann. Chem. 1994, 1121.
15. Selected symmetrical pyrrolo[3,2-b]pyrrole-2,5-diones have been prepared in three steps from (N-phenylacetyl)-acetic acid amino ester: (a) Bayer AG, a one step synthesis using pulvinic acid proceeded under harsh conditions (autoclave reaction, 140-180°C: Fürstenwerth, H. Ger. Offen., DE 3,525,109 A1, 1987; Chem. Abstr. 1987, 106, 103815f. (b) Ciba-Geigy: Rochat, A. C.; Iqbal, A.; Pfenninger, J.; Casser, L. Eur. Pat. Appl., EP 016309, 1984. See also: Solberg, Y. Z. Naturforsch. 1977, 32c, 292. Stachel, H.-D. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1962, 295, 735. (e) Mukai, T.; Konno, A.; Kumagai, T.; Satake, K. Chem. Lett. 1985, 1809. (f) Stachel, H.-D.; Schorp, M.; Maier, L.; Dandl, K. Liebigs Ann. Chem. 1994, 1121.
16. Selected symmetrical pyrrolo[3,2-b]pyrrole-2,5-diones have been prepared in three steps from (N-phenylacetyl)-acetic acid amino ester: (a) Bayer AG, a one step synthesis using pulvinic acid proceeded under harsh conditions (autoclave reaction, 140-180°C: Fürstenwerth, H. Ger. Offen., DE 3,525,109 A1, 1987; Chem. Abstr. 1987, 106, 103815f. (b) Ciba-Geigy: Rochat, A. C.; Iqbal, A.; Pfenninger, J.; Casser, L. Eur. Pat. Appl., EP 016309, 1984. (c) See also: Solberg, Y. Z. Naturforsch. 1977, 32c, 292. Stachel, H.-D. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1962, 295, 735. (e) Mukai, T.; Konno, A.; Kumagai, T.; Satake, K. Chem. Lett. 1985, 1809. (f) Stachel, H.-D.; Schorp, M.; Maier, L.; Dandl, K. Liebigs Ann. Chem. 1994, 1121.
17. Selected symmetrical pyrrolo[3,2-b]pyrrole-2,5-diones have been prepared in three steps from (N-phenylacetyl)-acetic acid amino ester: (a) Bayer AG, a one step synthesis using pulvinic acid proceeded under harsh conditions (autoclave reaction, 140-180°C: Fürstenwerth, H. Ger. Offen., DE 3,525,109 A1, 1987; Chem. Abstr. 1987, 106, 103815f. (b) Ciba-Geigy: Rochat, A. C.; Iqbal, A.; Pfenninger, J.; Casser, L. Eur. Pat. Appl., EP 016309, 1984. See also: Solberg, Y. Z. Naturforsch. 1977, 32c, 292. (d) Stachel, H.-D. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1962, 295, 735. (e) Mukai, T.; Konno, A.; Kumagai, T.; Satake, K. Chem. Lett. 1985, 1809. (f) Stachel, H.-D.; Schorp, M.; Maier, L.; Dandl, K. Liebigs Ann. Chem. 1994, 1121.
18. Selected symmetrical pyrrolo[3,2-b]pyrrole-2,5-diones have been prepared in three steps from (N-phenylacetyl)-acetic acid amino ester: (a) Bayer AG, a one step synthesis using pulvinic acid proceeded under harsh conditions (autoclave reaction, 140-180°C: Fürstenwerth, H. Ger. Offen., DE 3,525,109 A1, 1987; Chem. Abstr. 1987, 106, 103815f. (b) Ciba-Geigy: Rochat, A. C.; Iqbal, A.; Pfenninger, J.; Casser, L. Eur. Pat. Appl., EP 016309, 1984. See also: Solberg, Y. Z. Naturforsch. 1977, 32c, 292. Stachel, H.-D. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1962, 295, 735. (e) Mukai, T.; Konno, A.; Kumagai, T.; Satake, K. Chem. Lett. 1985, 1809. (f) Stachel, H.-D.; Schorp, M.; Maier, L.; Dandl, K. Liebigs Ann. Chem. 1994, 1121.
19. Selected symmetrical pyrrolo[3,2-b]pyrrole-2,5-diones have been prepared in three steps from (N-phenylacetyl)-acetic acid amino ester: (a) Bayer AG, a one step synthesis using pulvinic acid proceeded under harsh conditions (autoclave reaction, 140-180°C: Fürstenwerth, H. Ger. Offen., DE 3,525,109 A1, 1987; Chem. Abstr. 1987, 106, 103815f. (b) Ciba-Geigy: Rochat, A. C.; Iqbal, A.; Pfenninger, J.; Casser, L. Eur. Pat. Appl., EP 016309, 1984. See also: Solberg, Y. Z. Naturforsch. 1977, 32c, 292. Stachel, H.-D. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1962, 295, 735. (e) Mukai, T.; Konno, A.; Kumagai, T.; Satake, K. Chem. Lett. 1985, 1809. (f) Stachel, H.-D.; Schorp, M.; Maier, L.; Dandl, K. Liebigs Ann. Chem. 1994, 1121.
20. Langer, P.; Wuckelt, J.; Döring, M. J. Org. Chem. 2000, 65, 729.
21. Push-pull substituted heterocycles are of considerable importance. For a review, see: (a) Gompper, R.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1988, 27, 1437; Angew. Chem. 1988, 100, 1492. (b) See also: Effenberger, F.; Schlosser, H.; Bäuerle, P.; Maier, S.; Port, H.; Wolf, H. C. Angew. Chem., Int. Ed. Engl. 1988, 27, 281; Angew. Chem. 1988, 100, 274.
22. Push-pull substituted heterocycles are of considerable importance. For a review, see: (a) Gompper, R.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1988, 27, 1437; Angew. Chem. 1988, 100, 1492. (b) See also: Effenberger, F.; Schlosser, H.; Bäuerle, P.; Maier, S.; Port, H.; Wolf, H. C. Angew. Chem., Int. Ed. Engl. 1988, 27, 281; Angew. Chem. 1988, 100, 274.
23. Push-pull substituted heterocycles are of considerable importance. For a review, see: (a) Gompper, R.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1988, 27, 1437; Angew. Chem. 1988, 100, 1492. (b) See also: Effenberger, F.; Schlosser, H.; Bäuerle, P.; Maier, S.; Port, H.; Wolf, H. C. Angew. Chem., Int. Ed. Engl. 1988, 27, 281; Angew. Chem. 1988, 100, 274.
24. Push-pull substituted heterocycles are of considerable importance. For a review, see: (a) Gompper, R.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1988, 27, 1437; Angew. Chem. 1988, 100, 1492. (b) See also: Effenberger, F.; Schlosser, H.; Bäuerle, P.; Maier, S.; Port, H.; Wolf, H. C. Angew. Chem., Int. Ed. Engl. 1988, 27, 281; Angew. Chem. 1988, 100, 274.
25. Review: Langer, P.; Döring, M. Eur. J. Org. Chem. 2002, 221.
26. 2 (305.06): C, 62.99; H, 4.58; N, 9.17. Found: C, 63. 08; H, 4.96; N, 9.09. All new compounds gave satisfactory spectroscopic and analytical and/or high resolution mass data.
27. 2 (512.6): C, 79.66; H, 5.51; N, 5.46. Found: C, 79.19; H, 5.86; N, 5.37.
28. For symmetrical derivatives, see: Langer, P.; Wuckelt, J.; Döring, M.; Görls, H. Eur. J. Org. Chem. 2001, 1503.