A Novel Approach to Pyrrolo[2,1-b]thiazoles

Abstract

5-Aroyl-2-(dimethylamino)methylidene-2,3-dihydro-3-oxopyrrolo[2,1-b]thiazole-7-carboxylic acid esters, -7-carbonitriles and corresponding 7-hetaryl substituted derivatives were prepared. Thus, the substituted acetonitriles (XCH₂CN, where X = CO₂R, CN, hetaryl) were treated with mercaptoacetic acid yielding 2-(X-methylidene)thiazolidin-4-ones, which were N-alkylated with phenacyl bromides. Further formylation of the obtained compounds with excess of DMF·POCl₃ complex led to the above mentioned pyrrolo[2,1-b]thiazoles.

Key words

alkylations - heterocycles - pyrrolo[2,1-b]thiazoles - ring closure - 4-thiazolidinones

References

• 1a Khalil EM. Pradhan A. Ojala WH. Cleason WB. Mishra RK. Johnson RL. J. Med. Chem.  1999,  42:  2977 
• 1b Subashinghe NL. Bontems RJ. McIntee E. Mishra RK. Johnson RL. J. Med. Chem.  1993,  36:  2356 
• 2a Suzuki N, Nakayama A, Saijo T, Hasegawa M, and Yokohama S. inventors; Japanese Patent  04145086.  ; Chem. Abstr. 1992, 117, 212487
• 2b Suzuki N, Nakayama A, Hosokami TC, Hasegawa M, and Yokohama S. inventors; Spanish Patent  410224.  ; Chem. Abstr. 1991, 115, 49668
• 2c Suzuki N, Nakayama A, Hasegawa M, Yokohama S, and Saijo T. inventors; Japanese Patent  04261186.  ; Chem. Abstr. 1993, 118, 213095
• 2d Suzuki N, Nakayama A, Saijo T, Hasegawa M, Yokohama S, and Otsubo E. inventors; Japanese Patent  04208290.  ; Chem. Abstr. 1993, 118, 124527
• 2e Hasegawa M. Nakayama A. Yokohama S. Hosokami T. Kurebayashi Y. Ikeda T. Shimoto Y. Ide S. Honda Y. Suzuki N. Chem. Pharm. Bull.  1995,  43:  1125 
• 3a Padwa A. Chiacchio U. Venkatramanan MK. J. Chem. Soc., Chem. Commun.  1985,  1108 
• 3b Tsuge O. Kanemasa S. Takenaka S. Bull. Chem. Soc. Jpn.  1985,  3137 
• 3c Tsuge O. Kanemasa S. Takenaka S. Heterocycles  1983,  20:  1907 
• 3d Kraus GA. Nagy JO. Tetrahedron  1985,  41:  3537 
• 3e Kraus GA. Nagy JO. Tetrahedron Lett.  1981,  22:  2727 
• 4a Abe N. Nishiwaki T. Komoto N. Bull. Chem. Soc. Jpn.  1980,  53:  3308 
• 4b Abe N. Nishiwaki T. Komoto N. Chem. Lett.  1980,  223 
• 5a Farbe JL, Farge D, James C, and Lave D. inventors; Spanish Patent  147317.  ; Chem. Abstr. 1985, 103, 160500
• 5b Lalezari I. Schwartz EL. J. Med. Chem.  1988,  31:  1427 
• 5c Bacque E, Bashiardes G, Dereu N, and Nemecek C. inventors; PCT Int. Appl. WO  9700073.  ; Chem. Abstr. 1997, 126, 157394
• 6a Volovenko YuM. Volovnenko TA. Tverdokhlebov AV. Chem. Heterocycl. Compd. (Engl. Transl.)  2001,  37:  1011 
• 6b Volovenko YuM. Tverdokhlebov AV. Gorulya AP. Shishkina SV. Zubatyuk RI. Shishkin OV. Eur. J. Org. Chem.  2002,  4:  663 
• 7a Meyer H. Liebigs Ann. Chem.  1981,  1534 
• 7b Gupta AK. Ila H. Junjappa H. Synthesis  1988,  284 
• 7c Gupta AK. Chakrasali RT. Ila H. Junjappa H. Synthesis  1989,  141 
• 7d El-Shafei AK. El-Sayed AM. Abdel-Ghany H. Gazz. Chim. Ital.  1990,  120:  193 
• 7e Schafer H. Gewald K. J. Prakt. Chem.  1974,  316:  684 
• 8a Elnagdi MH. Elmoghayar RMH. Hammam AEFG. Khallaf SA. J. Heterocycl. Chem.  1979,  16:  1541 
• 8b Satzinger G. Liebigs Ann. Chem.  1978,  473 
• 8c Satzinger G. Liebigs Ann. Chem.  1963,  151 
• 8d Isidor JL. McKee RL. J. Org. Chem.  1973,  38:  3615 
• 8e Elnagdi MH. Khalifa MAE. Ibraheim MKA. Elmoghayar RMH. J. Heterocycl. Chem.  1981,  18:  877 
• 8f El-Shafei AK. El-Sayed AM. Soliman AM. Gazz. Chim. Ital.  1987,  117:  385 
• 9a Knoll A, Paetzel M, and Liebscher J. inventors; German Patent (East)  262863.  ; Chem. Abstr. 1989, 111, 153789
• 9b Knoll A. Liebscher J. Z. Chem.  1988,  28:  214 
• 10a Coulton S. Southgate R. J. Chem. Soc., Perkin Trans. 1  1992,  961 
• 10b Cheeseman GWH. Hawi AA. J. Heterocycl. Chem.  1983,  20:  591 
• 11 Balls AK. Kohler F. Ber. Dtsch. Chem. Ges.  1931,  64:  34 
• 12 Elnagdi MH. Abdallah SO. Ghoneim KM. Ebied EM. Kassab KN. J. Chem. Res., Miniprint  1997,  2:  375