Chemistry] Research Zone India Vol

ISSN 2319 - 8168 Science [Chemistry] Research Zone India Vol. 1 Issue - (4) Sept.- 2013 Page - 1-7 ISSN 2319 - 8168 * V. J. HUSHARE SYNTHESIS, CHARACTERIZATION OF SOME NOVEL HETEROCYCLES AND THEIR GROWTH PROMOTING EFFECT ON SOME FLOWERING PLANTS A series of chlorosubstituted 4-aroylpyrazolines have been synthesized by the interaction of chlorosubstituted-3-aroylflavanones and 3-alkoylchromanone with phenylhydrazine hydrochloride refluxing in dioxane medium with 0.5 ml of piperidine. Initially chlorosubstituted- 3-aroylflavanones and 3-alkoylchromanone have been prepared by the interaction of different aldehydes with 1(2-hydroxy-3,5-dichloropheny)-3-phenyl-1,3-propendione. Constitutions of synthesized compounds have been confirmed on the basis of elemental analysis, molecular weight determination, UV-Visible, I.R. and 1H-NMR spectral data. The synthesized compounds were evaluated for their growth promoting activity on some flowering plants viz. Papaver rhoeas, Dianthus chinensis, Candy tuft, Calendula officinalise, Gladiola tristis, Gaillardia. KEY WORDS: Synthesis of chlorosubstituted-3-aroylflavanones, 3-alkoylchromanone and pyrazolines. INTRODUCTION: tristis, Gaillardia. Heterocyclic compounds1 promote the life on EXPERIMENTAL: earth as they are widely distributed in nature The melting points of all synthesized and essential for the sustains of life. Any of compounds were recorded using hot paraffin the groups of heterocyclic compound bath and are uncorrected. Chemicals used containing three carbon atoms i.e. two were of A. R. Grade. 1H NMR spectra using adjacent nitrogen atom and one double bound CDCl3. I.R. spectra were recorded on Perkin- in the ring is pyrazolines. Pyrazoline Elmer spectrophotometer in the range 4000 derivatives have been found to possess a broad – 400 Cm-1 in nujol mull and as KBr pellets. spectrum of biological activities such as anti- UV-VIS spectrum was recorded in nujol inflamatory2, insecticidal3, anti-tuberculor4, medium. anti-tumor5, tranquilizing6, Synthesis of 2-benzoyloxy-3-5- immunosuppressive7, diuretic8, dichloroacetophenone (3a): anticonvulsant9, antifungal10, antidepressant 2-Hydroxy-3,5-dichloroacetophenone (2a) ( 11, antibacterial12, and molluscidal13. These 0.04Mmol) and benzoyl chlorides (0.05 mol) compounds successfully screened for their were dissolved in 10% NaOH (30 ml). The growth promoting impacts on some crop reaction mixture was shacked for about half plants viz. Papaver rhoeas, Dianthus chinensis, an hour. The products thus separated was Candy tuft, Calendula officinalise, Gladiola filtered washed with water followed by * Department of Chemistry, GVISH Amravati (Maharashtra) Research Zone India - 1, Vol. (IV) 4, September - 2013 [ 1 ] ISSN 2319 - 8168 sodium bicarbonate (10%) washing and then crystallized from ethanol. again with water. The solid product thus Similarly other compounds 3-(-2-hydroxy-3,5- separated was crystallized from ethanol. dichlorophenyl)-4-benzoly-5-(4- Synthesis of 1-(-2-hydroxy-3,5- chlorophenyl)-1-phenyl-”2-pyrazoline (6b) dichlorophenyl)-3-phenyl-1,3- and 3-(-2-hydroxy-3,5-dichlorophenyl)-4- propendione (4a) : benzoly-5-butyl-1-phenyl-”2-pyrazoline (6c) 2-Benzoyloxy-3,5-dichloroacetophenone (3a) were synthesized separately from the (0.05mol) was dissolved in dry pyridine (40 compounds (5b) and (5c) respectively. ml). The solution was warm up to 60°C and The synthesized compounds were pulverized KOH (15 gm) was added slowly with characterized on the basis of elemental constant stirring. The reaction mixture was analysis, molecular determination, U.V., kept for overnight and then acidified by adding I.R., N.M.R. spectral data. ice cold HCl (10%). The brownish yellow solid Compound (5a): Yield 75%, M.P. 90°C (Found product thus separated was filtered, washed C = 59.68, H = 2.86, O = 18.00, Cl = 15.96, with sodium bicarbonate solution (10%) and N = 3.10. Calculated for C22H13O5NCl2 C = 59.72, finally again with water. It was then H = 2.94, O = 18.09, Cl = 16.06, N = crystallized from ethanol to get the compound 3.16%) ëmax – 364 nm ( n à p*) IR cm-1 (4a). 3050.5 (C-H streaching in Ar) 1611.4 (C=O), Synthesis of 3-benzoyl-2-(4-nitrophenyl-)- 1473.9 (C-NO2), 1278 (-C-O), 1182.6 (-C-O) -1 6, 8-dichloroflavonone (5a): 717.7 cm (-C-Cl). ä(CDCl3 solvent) 6.75 A mixture of 1-(2-hydroxy-3, 5- (1H, d, -CH-CH) 6.9 (1H, d, -CH-CH), 6.875 – dichlorophenyl)-3-phenyl-1, 3-propendione 8.712 (11H, m, Ar-H). (4a) (0.01mol) and p-nitrobenzaldehyde Compound (5b): Yield70%, M.P. 120°C (0.02mol) was refluxed in dioxane (25 ml) (Found C = 61.10, H = 2.96, O = 11.00, Cl = containing (0.5 ml) piperidine for 15 – 20 min. 24.18, Calculated for C22H13O3Cl3 C = 61.18, H After cooling the reaction mixture was = 3.01, O = 11.12, Cl = 24.68 %) ëmax – acidified with dil. HCl (10%). The product thus 319 nm ( n à p*) IR cm-1 2928.6 (C-H separated was crystallized from ethanol to get streaching in Ar) 1612.6 (C=O), 1427.7 (C-H the compound (5a). in Ar), -1 Similarly 3-benzoyl-2-(4-chlorophenyl-)-6,8- 1086.5 (C-O), 764.6 cm (-C-Cl). ä(CDCl3 dichloroflavonone (5b) and 3-benzoyl-2-butyl- solvent) 6.76 (1H, d, -CH-CH) 6.79 (1H, d, - 6,8-dichloroflavonone (5c) were synthesized CH-CH), 6.926– 8.315 (11H, m, Ar-H). separately from the compound (4a) by using Compound (5c): Yield75%, M.P. 155°C p-chlorobenzaldehyde and valeraldehyde (Found C = 63.54, H = 4.50, O = 12.68, Cl = respectively. 18.75, Synthesis of 3-(-2-hydroxy-3, 5- Calculated for C20H18O3Cl2 C = 63.66, H = 4.77, dichlorophenyl)-4-benzoly-5-(4- O = 12.73, Cl = 18.83 %) ëmax – 363 nm ( nitrophenyl)-1-phenyl-”2-pyrazoline (6a): n à p*) IR cm-1 3068.7 (C-H streaching in Ar) A mixture of 3-benzoyl-2-(4-nitrophenyl)-6, 8- 2866.4 (C-H streaching in Ar), 2866.4 (C- dichloroflavanone (5a) (0.01 mol) and H in –(CH2)3-), 1689.5 (C=O), 1605.8 (C- H phenylhydrazine hydrochloride (0.02mol) was streaching in Ar) 1457.7 (-CH3 Bending), refluxed in dioxane (20 ml) containing 0.5 ml 1286.3 (C – O in ether), 705.4 cm-1 (-C-Cl). piperidine for two hours. After cooling the ä(CDCl3 solvent) 0.90 (3H, t, (CH2)3-CH3) 1.25 reaction mixture was diluted with water. The (2H, m (CH2)2-CH2 – CH3) 1.50 (2H, t, -CH2-CH2- product thus separated was filtered and CH2-CH3) 2.65 (2H, t, CH2-(CH2)2-CH3) [ 2 ] Research Zone India - 1, Vol. (IV) 4, September - 2013 ISSN 2319 - 8168 6.88 (1H, d, C-H), 6.93 (1H, d, C-H) 7.00 – 8.225 Scheme (7H, ,m, Ar-H). OCOCH3 OH Al Cl3 (C H3CO)2O Compound (6a): Yield 80%, M.P. 153°C 1200 C CH3COONa Cl (Found C = 63.10, H = 3.50, O = 12.00, N = 7.80, Cl I II Cl = 13.25, Calculated for C28H19O4N3Cl2 C = Cl 63.15, H = 3.57, O = 12.03, N = 7.89, Cl = OH OH -1 NaOH 10% Cl2 in Acet ic acid 13.34 %) ëmax – 341 nm ( n à p*) IR cm C6H5COCl Cl COCH3 COCH 3438.6 (Strong intermolecular H-bended O-H Cl 3 ( 2a ) streaching) 3071.8 (C-H streaching in Ar), (Ia ) Cl Cl 1598.2 (C=O), 1528 (C = N), 1348.2 (C – OCOC H 6 5 OH NO2) KOH / BVT R-CHO 1260.3 (-C-O), 751.4 cm-1 (-C-Cl). ä(CDCl Pyridene Ethenol ,Pyridine 3 Cl COCH3 Cl COCH2COC 6H5 solvent) 6.5 (1H, d, -CH-CH-) , 6.7 (1 H, d, - ( 3a ) ( 4a) CH-CH-) 6.80 – 8.98 (16 H, m, Ar–CH) 10.20 Cl O R Cl (1H, s, Ar-OH). Ph-NH-NH2-HCl OH Compound (6b): Yield 80%, M.P. 153°C Ethan ol, piperidin e Cl COC6H5 CO (Found C = 64.38, H = 3.60, O = 6.08, N = 5.30, O Cl (5a - -- 5c ) N Cl = 20.35, Calculated for C H O N Cl C = R 28 19 2 2 3 N 64.42, H = 3.64, O = 6.13, N = 5.36, Cl = 20.42 %) ëmax – 320 nm ( n à p*) IR cm-1 3287 (O-H) 1597 (C=O), 1248 (-C-O), 768.3 (6a----6c) cm-1 (-C-Cl). ä(CDCl solvent) 5.10 (1H, d, -CH- 3 Where R= C6H5-NO2, C6H5-Cl, -(CH2)3-CH3. CH-) , 5.90 (1 H, d, -CH-CH-) 6.24 – 8.20 Growth promoting effect on some (16 H, m, Ar–CH) 9.98 (1H, s, Ar-OH). flowering plants: Compound (6c): Yield 80%, M.P. 170°C The experimental set up of the study is divided (Found C = 66.74, H = 5.08, O = 6.80, N = 5.90, into, Cl = 15.10, Calculated for C26H24O2N2Cl2 C = i) Seed Treatment 66.80, H = 5.13, O = 6.85, N = 5.90, Cl = ii) Field Experiment 15.20 %) ëmax – 324 nm ( n à p*) IR cm-1 i) Seed Treatment :- With a view to safeguard 3421.3 (Ar O-H) 3060.1 (Ar - CH), 2924.4 dormant seed’s potential from harmful (CH in alkane) 1764.2 (C=O), 1602.5 (-C = N), external agencies, the seed of the test plants 1456.8 (CH2-bending) 1188.6 (C-O) 764.9 were treated by test compounds before -1 cm (-C-Cl). ä(CDCl3 solvent) 0.9 to 2.989 (9H, sowing. m, -(CH2)3-CH3), 6.59 – 8.465 (15 H, m, ii) Field Experiment :- Pre-germinated Ar–H) 13-14. quality seeds of Poppy, Pink, Candy tuft, Gaillardia Calendula, Gladiolus were procured from genuine agricultural agencies.

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