Synthesis of Novel Heterocyclic Compounds

Abstract

The present dissertation entitled “Synthesis of Novel Heterocyclic Compounds” is comprised of two parts. Part A describes the synthesis of Azaborines. In Part A the synthesis of Azaborines is classified into two classes. (a) 1, 3, 2 benzodiazaborininones (carbonyl containing, boron-based heterocyclic scaffolds) (68-89). In the synthesis of 1, 3, 2 benzodiazaborininones, anthranilamide reacted with different commonly available potassium organitriflouroborates using a fluorophile (BF3NH2Et) with efficient methodology. NH B NH O 68 F NH B NH O MeO OMe 69 NH B NH O O 70 NH B NH O 71 NH B NH O Br 72 NH B NH O F F 73 NH B NH O COOMe 74 NH B NH O CN 75 NH B NH O 76 NH B NH O O 77 NH B N H O CH3 78 Abstract ix NH B N H O CF3 79 NH B N H O S 80 NH B NH O NO2 81 NH B NH O 82 NH B NH O 83 84 NH B NH NH2 O NH B NH Cl O 85 NH B NH O CO2Me 86 CH2CO2Me NH B NH O 87 NH B NH O 88 N H B NH N O 89 The second class of azaborines prepared were 1,2-dihydroazaborinines, including 1-benzenyl-2-quinolinyl/isoquinolinyl-1,2-dihydroazaborinines (91-95, b1). These were obtained by reacting N-benzyl-2-vinylaniline with potassium organotrifouroborates in the presence of SiCl4 and Et3N. 2-Ethynyl-1,2-dihydroazaborinines (96-97, b2) were synthesized by using the same methodology where 2-vinylaniline was used with different commercially available potassium organotriflouroborates. All the products synthesized were charecterzied by FT-IR, 1H-NMR, 13C-NMR, 11B-NMR, HRMS. The results obtained confirmed the formation of desired product. Abstract x B N N B N N B N N B N N B N N 91 92 93 94 95 B HN TMS B HN F 96 97 Part B. Part B consists of the synthesis of 2,4 di-substituted quinolines. The 2, 4- disubstituted quinolines were synthesized using a Povarov related reaction using indium chloride as a catalyst. Two classes of 2,4 di-substituted quinolines were prepared. (c) Quinoline isoindolindiones (187-193) products were synthesized in two steps.The First step involved Schiff base synthesis while second step involved condensation of Schiff bases with N-propargylphthalimide. N Cl OMe N O O N Br OMe N O O N OMe N O O MeO 187 188 189 Abstract xi N OMe N O O N OMe N O O N Cl N O O MeO N N O O 190 191 192 193 Second class is (d) benzoquinoline isoindolindiones (194,195). These compounds were prepared by reacting aldehydes, 1-naphthyl amine with N-propargylphthalimide in presence of indium chloride catalyst. All these compounds were characterized through FT-IR, 1H-NMR and 13C-NMR. Along with N-propargylphthalimide, another alkyne, 1- nitro-4-(prop-2-ynyloxy)benzene was used under the same conditions. A reaction was attempted where 1-nitro-4-(prop-2-ynyloxy)benzene was reacted with benzo[c][1,2,5]thiadiazol-5-amine and different aldehydes, but the product isolated was not the desired one. N N O O N N O O 194 195