Journal
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
Volume 15, Issue 1, Pages 191-199Publisher
SPRINGER
DOI: 10.1007/s13738-017-1223-9
Keywords
2-(Piperidin-1-yl) acetamide; Pyrano[2,3-d] thiazoles; Pyrazoles
Categories
Funding
- Science and Technology Development Fund of Egypt (STDF)
Ask authors/readers for more resources
2-(-Piperidin-1-yl) acetamide (2) was easily prepared by reacting chloroacetonitrile with piperidine. Furthermore, (2) was allowed to react with different aromatic aldehydes to afford novel arylidene derivatives (3a,b). Unexpectedly, 2-oxo-4-hydroxy-thiazole (5) was obtained instead of 2-(piperidin-1-yl-methylene) thiazolidin-4-one (4) when (2) was treated with mercaptoacetic acid under fusion conditions. Subsequent treatment of (5) with aromatic aldehydes and either malononitrile or cyanoacetamide (1:1:1 molar ratios) produced the hitherto unknown pyrano[2,3-d] thiazole derivatives (6a,b) and (7). Novel pyrazole derivatives (8a, b) and (9) were synthesized upon cyclocondensation of (2) with aromatic aldehydes and hydrazine hydrate. Unfortunately, attempts to prepare novel isoxazole derivatives by utilizing hydroxylamine instead of hydrazine hydrate following the previous procedure were failed. Surprisingly, the uncyclized products (10a,b) were obtained rather than 3-hydroxy-4-piperidinyl-isoxazole (11a,b). Upon refluxing thiosemicarbazide with (2) and aromatic aldehydes under the same conditions, pyrazolinone carbothioamides (12), (13) and (14a-c) were obtained.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available