Figure 1: COSY spectrum of 4-methoxy substituted bicyclic adduct 3.
Acetoacetanilides were synthesized using transacetoacetylation method as given below. Aniline, 2-methoxyaniline or 4-methoxyaniline (0.1 mol) was refluxed with t-butylacetoacetate (0.15 mol) in xylene (25 ml) for 15-30 min. The reaction mixture was distilled to remove excess xylene. The concentrated coloured solution was cooled in an ice bath with continuous stirring. Ether (20 ml) was added and the resulting amorphous solid was filtered. This method of using t-butylacetoacetate [17] resulted in high yield within a short time. Yield ~80-85%, mp H-85°, 2-OCH 3 - 87 ° , 4-OCH 3 -114°. FT-IR (KBr) cm -1 of acetoacetanilide: 3338-3360 (N-H), 2912-2926 (C-H), 1720 (C=O), 1683 (C=O of amide), 1620-1625 (C=C), 1490-1495 (C-C) 1100-1120 (C-O).
The general procedure for the synthesis of bicyclic adducts triethylammonium {[7-hydroxy-4,9-dinitro-8-(4′ -/2′-methoxy/unsubstitutedphenylcarbamoyl)bicyclo[3.3.1]nona-3,7-dien-2-ylidene](oxido)-λ5 -azanyl}oxidanides were elaborated below. The bicyclic adducts (1-3) were synthesized [9],[18] from 1, 3, 5-trinitrobenzene and acetoacetanilide, 2-methoxy and 4-methoxy acetoacetanilides. A mixture of acetoacetanilide (0.01 mol) and 1, 3, 5-trinitrobenzene (0.01 mol) was warmed in absolute alcohol to dissolve the compounds. After cooling, a two to three fold excess of triethylamine was added and then mechanically stirred for 2-4 h. The intensely coloured residual liquid was kept overnight at 30-40° till bright orange solid or oily liquid separated out. The product was filtered or triturated with ether and the mother liquor was further treated with copious amounts of anhydrous ether and stirred in an ultrasonic bath for 15 min. The separated solid was combined with the filtered crystals, powdered well, washed with ethanol-ether solution and recrystallised from absolute alcohol. FT-IR (KBr) cm -1 of 1:3310-3320 (N-H), 2915-2920 (C-H), 1656-1648 (C=O), 1620-1623 (C=C), 1493-1496 (C-C), 1545-1549 (NO 2 asymm), 1400-1405 (NO 2 symm), 1085-1055 (C-O).
http://www.ijpsonline.com/article.asp?issn=0250-474X;year=2014;volume=76;issue=4;spage=370;epage=374;aulast=Chandrasekaran
 SHORT COMMUNICATION | |||||||||
| Year : 2014 | Volume : 76 | Issue : 4 | Page : 370-374 | |||||||||
| Comparative in vitro cytotoxic studies of novel 8-(4'/2'-Methoxy/Unsubstituted phenylcarbamoyl)bicyclo[3.3.1]nonane derivatives on ehrlich ascites carcinoma cell line | |||||||||
| Dhivya Chandrasekaran1, SAA Vandarkuzhali1, G Sridharan2, Radha Natarajan1, P Brindha3 1 Post Graduate and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli-620 002, India 2 Department of Biochemistry, Srimad Andavan Arts and Science College, Tiruchirappalli-620 005, India 3 Centre for Advanced Research in Indian System of Medicine (CARISM), Sastra University, Thanjavur-613 401, India
Correspondence Address: Radha Natarajan Post Graduate and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli-620 002 India | |||||||||
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