UGI 4-COMPONENT REACTION IS A KNOWN APPROACH TO ACCESS PSEUDOPEPTIDES. CHANGING ONE OF THE COMPONENTS IN UGI-4CR IS ONE OF THE GENERAL APPROACH TO ACCESS THE NOVEL FUNCTIONALIZED COMPOUNDS. DEVELOPING UGI-4CR TO ACCESS THE POLY FUNCTIONALIZED COMPOUNDS AND CARRYING OUT THE POST-TRANSFORMATION IS AN INTERESTING APPROACH IN ORGANIC SYNTHESIS. TO ACCESS THIS GOAL, A NOVEL CARBOXYLIC ACID WICH CONTAINED QUINAZOLINONE MOIETY WAS SYNTHESIZED. THE DESIRED CARBOXYLIC ACID WAS PREPARED THROUGH THREE-COMPONENT REACTION OF BOC-HYDRAZIDE, ISATOIC ANHYDRIDE AND PYRUVIC ACIDINETOH AS SOLVENT AND 30% H3PO3 AS ACIDIC CATALYST.QUINAZOLINONE DERIVATIVES WERE FOUND IN DIFFERENT BIOLOGICALLY ACTIVE COMPOUNDS AS ANTI HIV, ANTICANCER, ANTIHYPERTENSIVE, ANTIBACTERIAL, ANTIMUTAGENIC, ANTICOCCIDIAL, ANTICONVULSANT, ANTI-INFLAMMATORY, CNS DEPRESSANT, ANTIMALARIAL, ANTIOXIDANT, ANTILEUKEMIC ACTIVITY. HEREIN, WE REPORT THE SYNTHESIS OF A VIDE VARIETY OF QUINAZOLINONEPSEUDOPEPTIDESDERIVATIVES THROUGH A FOUR-COMPONENT UGI-4CR OF ALDEHYDES OR KETONES, AMINES, ISOCYANIDES, AND AN N -PROTECTED B-AMINO ACID WITH QUINAZOLINONE SKELETON. THE REACTION WAS CARRIED OUT SIMPLY AS ONE-POT PROTOCOL AT ROOM TEMPERATURE. THE PRODUCTS ARE MIXTURE OF DIASTEREOMERS WHICH WERE PURIFIED. THE STRUCTURE OF PRODUCTS WERE CONFIRMED BASED ON THE SPECTROSCOPIC DATA. INVESTIGATION OF THE BIOLOGICAL ACTIVITY OF THE PRODUCTS IS IN PROGRESS.

BACKGROUND: MULTICOMPONENT REACTION HAVE BECOME IMPORTANT TOOLS IN THE PREPARATION OF STRUCTURALLY DRIVERSE CHEMICAL LIBRARIES OF DRUG-LIKE POLYFUNCTIONAL COMPOUNDS. TO INSURE ACCESS TO FURTHER MOLECULAR DIVERSITY AND COMPLEXITY, CONTINUING EFFORTS ARE INVESTED TO DEVELOP NOVEL REACTIONS WITH HIGH EFFICIENCY, MINIMAL BY-PRODUCTS, AND HIGH SELECTIVITY IN NEW REACTION MEDIA [1]. 3-FORMYL CHROMONE IS A SUITABLE SUBSTRATE FOR THE SYNTHESIS OF HETEROCYCLIC SKELETONS. THIS COMPOUND HAS HIGH ACTIVITY DUE TO THREE ELECTROPHILIC CENTERS [2]. IN MOST CASES, THE CHROMONE SKELETON COULD BE OPENED THEREFORE THE DEVELOPMENT OF A FACILE APPROACH TO ACCESS THE NEW FUNCTIONALIZED COMPOUNDS WHICH CONTAINED CHROMONE SKELETON IS HIGHLY DESIRABLE AND VALUABLE FOR ORGANIC SYNTHESIS AND MEDICINAL CHEMISTRY.METHODS: A MIXTURE OF 3-FORMYL CHROMONE AND MALONONITRILE WAS HEATED IN DCE IN THE PRESENCE OF TRIETHYLAMINE (10%) AND THE DESIRED ALKENE WAS PRECIPITATED. THE SOLID WAS SEPARATED AND THEN MIXTURE OF ISOCYANIDE (1MMOL) AND DIMETHYL ACETYLENEDICARBOXYLATE WAS ADDED IN DCE AND THE MIXTURE WAS HEATED FOR 6H. FURTHER PURIFICATION WAS DONE USING PTLC AND DESIRED PRODUCT WERE OBTAINED 60-75% YIELD.RESULTS: IN CONTINUATION OF OUR RESEARCH WORK TO DESIGN OF NOVEL MULTICOMPONENT REACTIONS [3], WE WISH TO REPORT FOUR-COMPONENT REACTION APPROACH FOR THE SYNTHESIS OF POLYFUNCTIONALIZED CYCLOPENTADIENES CONTAINED CHROMONE SKELETON. THE STRUCTURE OF PRODUCTS WAS CONFIRMED BASED ON SPECTROSCOPIC DATA. THE REACTION COULD BE PROCEED THROUGH SEQUENTIAL KNOEVENAGEL/ MICHAEL/ CYCLIZATION REACTIONS. THE DETAILS ABOUT THE MECHANISM OF REACTION WILL DISCUSSED IN THE CONFERENCE.CONCLUSION: AN EFFICIENT APPROACH WAS DEVELOPED TO ACCESS POLYSUBSTITUTED CYCLOPENTADIENE DERIVATIVES WHICH CONTAINED CHROMONE MOIETY. GOOD TO HIGH YIELDS, HIGH BOND-FORMING EFFICIENCY ARE ADVANTAGE OF OUR APPROACH.

MANY PYRAZOLE DERIVATIVES ARE ACKNOWLEDGED TO POSSESS A WIDE RANGE OF BIOACTIVITIES. THE PYRAZOLE MOTIF MAKES UP THE CORE STRUCTUREOF NUMEROUS BIOLOGICALLY ACTIVE COMPOUNDS. MUCH ATTENTION WAS PAID TO PYRAZOLE AS A POTENTIAL ANTIMICROBIAL AGENT AFTER THE DISCOVERY OF THE NATURAL PYRAZOLE C-GLYCOSIDE, PYRAZOFURIN WHICH DEMONSTRATED A BROAD SPECTRUM OF ANTIMICROBIAL ACTIVITY...