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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/3049
Title: Reactions of 4-isothiocyanato-4-methyl-2- pentanone with amines having functional group at position and anti-inflammatory evaluation of resulting heterocyclic compounds
Authors: Sahu R.K.
Magan A.
Gupta B.
Sondhi S.M.
Published in: Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract: The reaction of 4-isothiocyanato-4-methyl-2-pentanone with o-phenylenediamine at room temperature yielded isomeric mixture of l-(2'-aminophenyl)-4, 4, 6-trimethyl-l, 4, 5, 6-tetrahydro-6-hydroxypyrimidine-2(3H)-thione (I), which on refluxing in MeOH with catalytic amount of sulphuric acid cyclizes to yield the known pyrimidobenzimidazole (IIa). The same product was also obtained by direct condensation of o-phenylenediamine with 4-isothiocyanato-4-methyl-2-pentanone in the presence of catalytic amount of acid and heating under reflux for 8 h. The reaction of 4-nitro-l, 2-phenylenediamine with 4- isothiocyanato-4-methyl-2-pentanone gave IIb. The reaction of o-aminophenol with 4-isothiocyanato-4-methyl-2-pentanone at pH 4.3 gave l-(2'-hydroxyphenyl)-4, 4, 6-trimethyl-l, 4-dihydro-pyrimidine-2(3H) thione (III), however the same reaction under strongly acidic conditions (pH 1) gave the known pyrimidobenzoxazole (IV). The reaction of 4-isothiocyanato-4-methyl-2-pentanone with o-aminothio-phenol and 2-amino ethanol under different pH conditions gave the known heterocycles V and VI, respectively. The structures of these compounds are supported by IR, 1 H NMR and HRMS. Antiinflammatory evaluation of I, IIa, IIb, III, IV, V and VI at 100 mg/kg showed that compounds I, IIa, III, and IV are inactive whereas, compounds IIb, V and VI showed 13%, 11%, and 21% activity, respectively. © 1994, Taylor & Francis Group, LLC. All rights reserved.
Citation: Phosphorus, Sulfur, and Silicon and the Related Elements (1994), 88(43834): 45-51
URI: https://doi.org/10.1080/10426509408036905
http://repository.iitr.ac.in/handle/123456789/3049
Issue Date: 1994
Keywords: amines
anti-inflammatory activity
heterocyclic
HRMS
Isothiocyanato pentanone
NMR
ISSN: 10426507
Author Scopus IDs: 7006054505
6507176182
7402195167
7006090710
Author Affiliations: Sahu, R.K., Chemistry Department, University of Roorkee, Roorkee-247 667 (U. P.), India, Department of Pharmacology, CDRI, Lucknow, (U. P.), India
Magan, A., Chemistry Department, University of Roorkee, Roorkee-247 667 (U. P.), India, Department of Pharmacology, CDRI, Lucknow, (U. P.), India
Gupta, B., Chemistry Department, University of Roorkee, Roorkee-247 667 (U. P.), India
Sondhi, S.M., Chemistry Department, University of Roorkee, Roorkee-247 667 (U. P.), India
Appears in Collections:Journal Publications [CY]

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