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Vol. 27 No. 10 (2015): Vol 27 Issue 10

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Synthesis of Novel Pyridazinonylbenzotriazoles

https://doi.org/10.14233/ajchem.2015.18894
S. Shashidhar Reddy
CiVenti Chem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad- 500 055, India
B. George Vineel
CiVenti Chem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad- 500 055, India
S. Venkataiah
CiVenti Chem (India) Private Limited, Plot No-72/A, Part-2, Phase-1, IDA Jeedimetla, Hyderabad- 500 055, India
A. Naidu
Department of Chemistry, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad-500 085, India
P.K. Dubey
Department of Chemistry, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : S. Shashidhar Reddy

shagum09@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 10 (2015): Vol 27 Issue 10

Abstract

4-Chlorobenzaldehyde (1) was reacted with crotononitrile (2) in the presence of sodium cyanide yielding 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile (3) which on refluxing with concentrated HCl gave 4-(4-chlorophenyl)-3-methyl-4-oxobutyric acid (4). The latter, on treatment with fuming nitric acid, yielded 4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid (5), which on treatment with hydrazine hydrate gave 6-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazine-3-one (6). Azidation and reduction of 6 with sodium azide gave the amino derivative 7 which on reductive alkylation gave 10(a-i) followed by reduction with commercially available sodium hydrogen sulphide solution gave the substituted diamine derivative 11(a-i). The compound 7 directly undergoes reduction with sodium hydrogen sulphide yielding (8). Finally, 8 and 11(a-i) was converted into the target compounds by diazotized-cyclization with sodium nitrite giving pyridazinonylbenzotriazoles 9 and 12( a-i).

Keywords

Pyridazinone Benzotriazole Michael addition Hydrazinolysis Diazotized-cyclization Pyridazinonyl derivatives
Shashidhar Reddy, S., George Vineel, B., Venkataiah, S., Naidu, A., & Dubey, P. (2015). Synthesis of Novel Pyridazinonylbenzotriazoles. Asian Journal of Chemistry, 27(10), 3633–3638. https://doi.org/10.14233/ajchem.2015.18894
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