Document Type: Original Research Article

Author

1 Department of Chemistry, Maku Branch, Islamic Azad University, Maku, 58619-93548, Iran

2 Young Researchers and Elite Club, Maku Branch, Islamic Azad University, Maku,58619-93548, Iran

10.33945/SAMI/PCBR.2019.2.3439

Abstract

The reaction of indoles with the complex formed from tertiary cyclic amides and phosphorus oxychloride, followed by basification using sodium hydroxide, was studied. In the case of five member amide rings, 3-(1-alkyl-pyrrolidine-2-ylidene)3H-indoles were obtained but in the case of six and seven member amide rings, ring opening was occurred and amino ketones were obtained.

Graphical Abstract

Keywords

Main Subjects

[[1]] Vilsmeier A., Haack A., Berichte der Deutschen Chemischen Gesellschaft, 1927, 60:119

[2] (a) Smith G.F., Journal of the Chemical Society, 1954, 1:3842 (b) James P.N., Snyder H.R., organic synthesis collective, 1963, 4:539

[3] Anthony W. C., Journal of Organic Chemistry, 1960, 25:2049

[4] Youngdale G.A., Anger D.G., Anthony W.C., Da Vanzo J.P., Greig M.E., Heinzelman R.V., Keasling H.H., Szmuszkovicz J., Journal of Medicinal Chemistry,1964, 7:415

[5] Harris M., Joule J.A., Journal of Chemical Research, 1978, 470

[6] Bishop D.I., Al-Khawaja I.K., Joule J.A., Journal of Chemical Research, 1981, 4279

[7] Bishop D.I., Al-Khawaja I.K., Heatley F., Journal of Chemical Research, 1982, 1766

[8] Al-Khawaja I.K., Beddoes R.L., Bishop D.I., Journal of Chemical Research, 1984, 2738

[9] Helliwell M., Aghazadeh M., Baradarani M.M., Joule J.A., Acta Crystallographica, 2009, E65:o3114

[10] Aghazadeh M., Baradarani M.M., Helliwell M., Mediterranean Journal of Chemistry, 2011, 1:98

[11] Aghazadeh M., Badali M., Baradarani M.M., ChimicaOggi-Chemistry Today, 2016, 34:34

[12] Aghazadeh M., Raftery J., Baradarani M.M., Joule J.A., Arkivoc, 2012, 7:158

[13] Helliwell M., Aghazadeh M., Baradarani M.M., Joule J.A., Acta Crystallographica, 2010, E66:o1532

[14] Sajjadifar S., Mansouri G., Miraninezhad S., Asian Journal of Nanoscience and Materials, 2018, 1:11

[15] Divar M., Khabnadideh S., Sabet R., Zomorodian K., Ershadi N., Hassanpour F., Chemical Methodologies, 2019,3:237