{"title":"用三乙胺从亚胺和盐酸合成新型顺式-2-氮杂环丁酮。","authors":"Handan Can Sakarya, Aslı Ketrez","doi":"10.17344/acsi.2023.8451","DOIUrl":null,"url":null,"abstract":"<p><p>A novel series of cis-2-azetidinones 2(a-c ) was carried out by the cyclo addition reaction of imine 1(a-c ) and acyl chloride in dry dichloromethane at 0-5 oC using triphenylamine. The cyclo addition of the Schiff bases with chloroacetyl chloride resulted corresponding major product cis-2-azetidinone stereoisomers 2(a-c). The synthesized compounds were characterized by analytical and spectral (Infrared, 1H NMR, 13C NMR, and elemental analysis) data. Keywords: Benzothiazole, β-lactam, Schiff base, cis-2-azetidinone, Staudinger reaction Acknowledgements The authors would like to thank the Eskişehir Osmangazi University Scientific Research Projects Council for financial support (Project No: 2014/19A208). References • C. M. L. Delpiccolo, M. A. Fraga, E. G. Mata, J. Comb. Chem. 2003, 5, 208-210. DOI: 10.1021/cc020107d. • R. B. Pawar, V. V. Mulwad, Chem. Heterocycl. Compd. 2004, 40, 219-226. DOI: 10.1023/B:COHC.0000027896.38910.d1. • P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur. J. Med. Chem. 2010, 45, 5541-5560. DOI: 10.1016/j.ejmech.2010.09.035. • G. S. Singh, B. J. Mmolotsi, Il Farmaco, 2005, 60, 727-730. DOI: 10.1016/j.farmac.2005.06.008. • C. D. Risi, G. P. Pollini, A. C. Veronese, V. Bertolasi, Tetrahedron Lett. 1999, 40, 6995-6998. DOI: 10.1016/S0040-4039(99)01421-5. • H. G. I. Georg: The Organic Chemistry of β-Lactams, Weinheim/VCH Publishers, New York, 1993, p. 295. DOI: 10.1002/ange.19941060738. • R. F. Abdulla, K. H. Fuhr, J. Med. Chem. 1975, 18, 625-627. DOI: 10.1021/jm00240a022. • W. Dürckheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202. DOI: 10.1002/anie.198501801. • P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur. J. Med. Chem. 2010, 45, 5541-5560. DOI: 10.1016/j.ejmech.2010.09.035. • H. Staudinger, Justus Liebigs Ann. Chem. 1907, 356, 51-123. DOI: 10.1002/jlac.19073560106. • A. K. Bose, M. Jayaraman, A. Okawa, S. S. Bari, E. W. Robb, M. S. Manhas, Tetrahedron Lett. 1996, 37, 6989-6992. DOI: 10.1016/0040-4039(96)01571-7. • A. K. Bose, B. K. Banik, M. S. Manhas, Tetrahedron Lett. 1995, 36, 213-216. DOI: 10.1016/0040-4039(94)02225-Z. • A. Arrieta, B. Lecea, F. P. Cossio, J. Org. Chem. 1998, 63, 5869-5876. DOI: 10.1021/jo9804745. • P. Vicini, A. Geronikaki, M. Incerti, B. Busonera, G. Poni, C. A. Cabras, P. L. Colla, Bioorg. Med. Chem. 2003, 11, 4785-4789. DOI: 10.1016/S0968-0896(03)00493-0. • K. Mogilaiah, R. B. Rao, K. N. Reddy, Indian J. Chem. 1999, 38B, 818-822. • 16. I. Georg, V. T. G. I. Ravikumar, Ed. Verlag Chemie, 1993, 295- 368 New York, • L. Jiao, Y. Liang, J. Xu. J. Am. Chem. Soc. 2006, 128, 6060- 6069 • H. C. Sakarya, M. Yandımoğlu, Croat. Chem. Acta, 2018, 91, 533-541. DOI: 10.5562/cca3386. • D. A. Nelson, J. Org. Chem. 1972, 37, 1447-1449. DOI: 10.1021/jo00974a038. • K. D. Barrow, T. M. Spotswood, Tetrahedron Lett. 1965, 6, 3325-3335. DOI: 10.1016/S0040-4039(01)89203-0. • J. Decazes, J. L. Luche, H. B, Kagan, Tetrahedron Lett. 1970, 11, 3665-3668. DOI: 10.1016/S0040-4039(01)98556-9. • D. A. Nelson, Tetrahedron Lett. 1971, 12, 2543-2546. DOI: 10.1016/S0040-4039(01)96914-X.</p>","PeriodicalId":7122,"journal":{"name":"Acta Chimica Slovenica","volume":"70 4","pages":"628-633"},"PeriodicalIF":1.2000,"publicationDate":"2023-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of Novel cis-2-Azetidinones from imines and aclychloride using triethylamine.\",\"authors\":\"Handan Can Sakarya, Aslı Ketrez\",\"doi\":\"10.17344/acsi.2023.8451\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A novel series of cis-2-azetidinones 2(a-c ) was carried out by the cyclo addition reaction of imine 1(a-c ) and acyl chloride in dry dichloromethane at 0-5 oC using triphenylamine. The cyclo addition of the Schiff bases with chloroacetyl chloride resulted corresponding major product cis-2-azetidinone stereoisomers 2(a-c). The synthesized compounds were characterized by analytical and spectral (Infrared, 1H NMR, 13C NMR, and elemental analysis) data. Keywords: Benzothiazole, β-lactam, Schiff base, cis-2-azetidinone, Staudinger reaction Acknowledgements The authors would like to thank the Eskişehir Osmangazi University Scientific Research Projects Council for financial support (Project No: 2014/19A208). References • C. M. L. Delpiccolo, M. A. Fraga, E. G. Mata, J. Comb. Chem. 2003, 5, 208-210. DOI: 10.1021/cc020107d. • R. B. Pawar, V. V. Mulwad, Chem. Heterocycl. Compd. 2004, 40, 219-226. DOI: 10.1023/B:COHC.0000027896.38910.d1. • P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur. J. Med. Chem. 2010, 45, 5541-5560. DOI: 10.1016/j.ejmech.2010.09.035. • G. S. Singh, B. J. Mmolotsi, Il Farmaco, 2005, 60, 727-730. DOI: 10.1016/j.farmac.2005.06.008. • C. D. Risi, G. P. Pollini, A. C. Veronese, V. Bertolasi, Tetrahedron Lett. 1999, 40, 6995-6998. DOI: 10.1016/S0040-4039(99)01421-5. • H. G. I. Georg: The Organic Chemistry of β-Lactams, Weinheim/VCH Publishers, New York, 1993, p. 295. DOI: 10.1002/ange.19941060738. • R. F. Abdulla, K. H. Fuhr, J. Med. Chem. 1975, 18, 625-627. DOI: 10.1021/jm00240a022. • W. Dürckheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202. DOI: 10.1002/anie.198501801. • P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur. J. Med. Chem. 2010, 45, 5541-5560. DOI: 10.1016/j.ejmech.2010.09.035. • H. Staudinger, Justus Liebigs Ann. Chem. 1907, 356, 51-123. DOI: 10.1002/jlac.19073560106. • A. K. Bose, M. Jayaraman, A. Okawa, S. S. Bari, E. W. Robb, M. S. Manhas, Tetrahedron Lett. 1996, 37, 6989-6992. DOI: 10.1016/0040-4039(96)01571-7. • A. K. Bose, B. K. Banik, M. S. Manhas, Tetrahedron Lett. 1995, 36, 213-216. DOI: 10.1016/0040-4039(94)02225-Z. • A. Arrieta, B. Lecea, F. P. Cossio, J. Org. 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引用次数: 0
摘要
亚胺 1(a-c ) 和酰氯在干燥的二氯甲烷中于 0-5 oC 温度下用三苯胺进行环加成反应，生成了一系列新型的顺式-2-氮杂环丁酮 2(a-c)。希夫碱与氯乙酰氯的环加成反应产生了相应的主要产物顺式-2-氮杂环丁酮立体异构体 2(a-c)。合成的化合物通过分析和光谱（红外光谱、1H NMR、13C NMR 和元素分析）数据进行了表征。关键词：苯并噻唑苯并噻唑 β-内酰胺 希夫碱 顺式-2-氮杂环丁酮 施陶丁格反应 致谢 作者感谢埃斯基谢希尔-奥斯曼加齐大学科研项目委员会的资助（项目编号：2014/19A208）。参考文献 - C. M. L. Delpiccolo, M. A. Fraga, E. G. Mata, J. Comb.Chem.2003, 5, 208-210.DOI: 10.1021/cc020107d.- R. B. Pawar, V. V. Mulwad, Chem.Heterocycl.Compd.2004, 40, 219-226.DOI: 10.1023/B:COHC.0000027896.38910.d1.- P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur.J. Med.Chem.2010, 45, 5541-5560.DOI: 10.1016/j.ejmech.2010.09.035.- G. S. Singh, B. J. Mmolotsi, Il Farmaco, 2005, 60, 727-730.DOI: 10.1016/j.farmac.2005.06.008.- C. D. Risi, G. P. Pollini, A. C. Veronese, V. Bertolasi, Tetrahedron Lett.1999, 40, 6995-6998.DOI: 10.1016/S0040-4039(99)01421-5.- H. G. I. Georg：The Organic Chemistry of β-Lactams, Weinheim/VCH Publishers, New York, 1993, p. 295.DOI: 10.1002/ange.19941060738.- R. F. Abdulla, K. H. Fuhr, J. Med.Chem.1975, 18, 625-627.DOI: 10.1021/jm00240a022.- W. Dürckheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew.Chem.Int.Ed. Engl.1985，24，180-202。DOI: 10.1002/anie.198501801.- P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur.J. Med.Chem.2010, 45, 5541-5560.DOI: 10.1016/j.ejmech.2010.09.035.- H. Staudinger, Justus Liebigs Ann.Chem.1907, 356, 51-123.DOI: 10.1002/jlac.19073560106.- A. K. Bose, M. Jayaraman, A. Okawa, S. S. Bari, E. W. Robb, M. S. Manhas, Tetrahedron Lett.1996, 37, 6989-6992.DOI: 10.1016/0040-4039(96)01571-7.- A. K. Bose, B. K. Banik, M. S. Manhas, Tetrahedron Lett.1995, 36, 213-216.DOI: 10.1016/0040-4039(94)02225-Z.- A. Arrieta, B. Lecea, F. P. Cossio, J. Org.Chem.1998, 63, 5869-5876.DOI: 10.1021/jo9804745.- P. Vicini, A. Geronikaki, M. Incerti, B. Busonera, G. Poni, C. A. Cabras, P. L. Colla, Bioorg.Med.Chem.2003, 11, 4785-4789.DOI: 10.1016/S0968-0896(03)00493-0.- K. Mogilaiah, R. B. Rao, K. N. Reddy, Indian J. Chem.1999, 38B, 818-822.- 16.I. Georg, V. T. G. I. Ravikumar, Ed.Verlag Chemie, 1993, 295- 368 New York, - L. Jiao, Y. Liang, J. Xu.J. Am.J. Am. Chem.2006, 128, 6060- 6069 - H. C. Sakarya, M. Yandımoğlu, Croat.Chem.Acta, 2018, 91, 533-541.DOI: 10.5562/cca3386.- D. A. Nelson, J. Org.Chem.1972, 37, 1447-1449.DOI: 10.1021/jo00974a038.- K. D. Barrow, T. M. Spotswood, Tetrahedron Lett.1965, 6, 3325-3335.DOI: 10.1016/S0040-4039(01)89203-0.- J. Decazes, J. L. Luche, H. B, Kagan, Tetrahedron Lett.1970, 11, 3665-3668.DOI: 10.1016/S0040-4039(01)98556-9.- D. A. Nelson, Tetrahedron Lett.1971, 12, 2543-2546.DOI: 10.1016/S0040-4039(01)96914-X.
Synthesis of Novel cis-2-Azetidinones from imines and aclychloride using triethylamine.
A novel series of cis-2-azetidinones 2(a-c ) was carried out by the cyclo addition reaction of imine 1(a-c ) and acyl chloride in dry dichloromethane at 0-5 oC using triphenylamine. The cyclo addition of the Schiff bases with chloroacetyl chloride resulted corresponding major product cis-2-azetidinone stereoisomers 2(a-c). The synthesized compounds were characterized by analytical and spectral (Infrared, 1H NMR, 13C NMR, and elemental analysis) data. Keywords: Benzothiazole, β-lactam, Schiff base, cis-2-azetidinone, Staudinger reaction Acknowledgements The authors would like to thank the Eskişehir Osmangazi University Scientific Research Projects Council for financial support (Project No: 2014/19A208). References • C. M. L. Delpiccolo, M. A. Fraga, E. G. Mata, J. Comb. Chem. 2003, 5, 208-210. DOI: 10.1021/cc020107d. • R. B. Pawar, V. V. Mulwad, Chem. Heterocycl. Compd. 2004, 40, 219-226. DOI: 10.1023/B:COHC.0000027896.38910.d1. • P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur. J. Med. Chem. 2010, 45, 5541-5560. DOI: 10.1016/j.ejmech.2010.09.035. • G. S. Singh, B. J. Mmolotsi, Il Farmaco, 2005, 60, 727-730. DOI: 10.1016/j.farmac.2005.06.008. • C. D. Risi, G. P. Pollini, A. C. Veronese, V. Bertolasi, Tetrahedron Lett. 1999, 40, 6995-6998. DOI: 10.1016/S0040-4039(99)01421-5. • H. G. I. Georg: The Organic Chemistry of β-Lactams, Weinheim/VCH Publishers, New York, 1993, p. 295. DOI: 10.1002/ange.19941060738. • R. F. Abdulla, K. H. Fuhr, J. Med. Chem. 1975, 18, 625-627. DOI: 10.1021/jm00240a022. • W. Dürckheimer, J. Blumbach, R. Lattrell, K. H. Scheunemann, Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202. DOI: 10.1002/anie.198501801. • P. D. Mehta, N. P. S. Sengar, A. K. Pathak, Eur. J. Med. Chem. 2010, 45, 5541-5560. DOI: 10.1016/j.ejmech.2010.09.035. • H. Staudinger, Justus Liebigs Ann. Chem. 1907, 356, 51-123. DOI: 10.1002/jlac.19073560106. • A. K. Bose, M. Jayaraman, A. Okawa, S. S. Bari, E. W. Robb, M. S. Manhas, Tetrahedron Lett. 1996, 37, 6989-6992. DOI: 10.1016/0040-4039(96)01571-7. • A. K. Bose, B. K. Banik, M. S. Manhas, Tetrahedron Lett. 1995, 36, 213-216. DOI: 10.1016/0040-4039(94)02225-Z. • A. Arrieta, B. Lecea, F. P. Cossio, J. Org. Chem. 1998, 63, 5869-5876. DOI: 10.1021/jo9804745. • P. Vicini, A. Geronikaki, M. Incerti, B. Busonera, G. Poni, C. A. Cabras, P. L. Colla, Bioorg. Med. Chem. 2003, 11, 4785-4789. DOI: 10.1016/S0968-0896(03)00493-0. • K. Mogilaiah, R. B. Rao, K. N. Reddy, Indian J. Chem. 1999, 38B, 818-822. • 16. I. Georg, V. T. G. I. Ravikumar, Ed. Verlag Chemie, 1993, 295- 368 New York, • L. Jiao, Y. Liang, J. Xu. J. Am. Chem. Soc. 2006, 128, 6060- 6069 • H. C. Sakarya, M. Yandımoğlu, Croat. Chem. Acta, 2018, 91, 533-541. DOI: 10.5562/cca3386. • D. A. Nelson, J. Org. Chem. 1972, 37, 1447-1449. DOI: 10.1021/jo00974a038. • K. D. Barrow, T. M. Spotswood, Tetrahedron Lett. 1965, 6, 3325-3335. DOI: 10.1016/S0040-4039(01)89203-0. • J. Decazes, J. L. Luche, H. B, Kagan, Tetrahedron Lett. 1970, 11, 3665-3668. DOI: 10.1016/S0040-4039(01)98556-9. • D. A. Nelson, Tetrahedron Lett. 1971, 12, 2543-2546. DOI: 10.1016/S0040-4039(01)96914-X.
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