SVIBOR - Project code: 1-07-039

MINISTRY OF SCIENCE AND TECHNOLOGY

Strossmayerov trg 4, HR - 10000 ZAGREB
tel.: +385 1 459 44 44, fax: +385 1 459 44 69
E-mail: ured@znanost.hr

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Project code: 1-07-039


CHEMISTRY AND PHOTOCHEMISTRY OF HETEROCYCLIC AND AROMATIC COMPOUNDS


Main researcher: JAKOPČIĆ, KREŠIMIR (17793)


Assistants
Type of research: basic
Duration from: 01/01/91. to 12/31/94.
Papers on project (total): 79
Papers on project quoted in Current Contents: 24
Institution name: Fakultet kemijskog inženjerstva i tehnologije, Zagreb (125)
Department/Institute: Department of Organic Chemistry
Address: Marulićev trg 20
City: 10000 - Zagreb, Croatia
Communication
Phone: 385 (0)01 45 52 477
Fax: 385 (0)01 45 50 725
Summary: As a part of our steady interest in the preparation of novel compounds with potential biological (preferably pharmacological) activity or technologically useful properties (dyestuffs, chelators, vulcanisators etc.), in a creation of new thermochemical or photochemical syntheses and study of mechanisms of these reactions, several types of organic molecules have been investigated. Our efforts resulted in: Better understanding of intramolecular /4+2/cycloadditions (IMDA-reaction) and aromatization of tetrahydroepoxyisoindolines obtained as the result of intramolecular DIELS-ALDER reaction of tertiary alkenyl-furfuryl-aryl-amines, and synthesis of new examples; Syntheses of novel formyl-derivatives of oxazoles, their intermolecular Diels-Alder reaction and their aminolytical transformation to pyrimidones; Contractions of 4-pyrone to cyclopentenone and/or pyrrole rings; Aminolytical transformatins of 4-pyrones to 4-pyridones; Oxidation of thioamides derived from 5-nitro-2-furoic acid and synthesis of thionamides of aliphatic alpha-hydroxy-carboxylic acids; Synthesis of vinylogous phenylfuryl-benzothiazoles and the influence of structural changes to absorption and fluorescence; Studies of inter- and intramolecular photoadditions of heteroaryl-divinylbenzenes (furyl, oxazolyl, pyrrolyl); Photodehydrocyclizations of distyryl-furans and thiophenes; Photochemical reactions of 4-pyrones and 4-pyridones, especially photodimerization of styryl-4-pyrones; Regiospecific synthesis of semibullvalenes; Separation of enantiomers by HPLC and thermodynamics of racemization; Synthesis of sydnones and sydnonyl-derivatives of erithromicilamine.

Keywords: Diels-Alder reaction, Intramolecular /4+2/cycloaddition, IMDA reaction, Oxidation, 5-Nitro-2-furyl-thiocarbonamides, Diimidoyl-disulphydes, alpha-Hydroxy-thiocarbonamides, Photocycloaddition, Photocyclodimerization, Photochemistry, Photoaddition, Photodehydrocyclization, Rearrangement, Fluorescence, Heterocycles, Furan, Thiophene, Pyrrole, Oxazole, Epoxyisoindoline, Isoindoline, Divinylbenzene, Quinolone, Benzothiazole, Vitamine B6, Thio compounds, 4-Pyrone, 4-Pyridone, Cyclopentenone, Erithromicylamine, Sydnone, Dibenzosemibullvalene, Separation of enantiomers.

Research goals: Using chemical and photochemical methods a number of new mono- and polycyclic carbo- and heterocyclic compounds will be prepared. Beside biologically and pharmacologically, technologically or otherwise useful compounds a better understanding of mechanisms and reactivity of used organic thermo- and photochemical reactions are expected. Special effort will be undertaken in finding new syntheses and structural characterizations of various molecules, especially those of heterocyclic type, and to studies of photochemical reactions, often superior alternatives of usual thermochemical methods. In particular, the studies will be performed as several more or less connected parts: (a)-Studies of substituent influence on the rate and stereochemistry of intramolecular Diels-Alder (IMDA) reaction of alkenylfurfurylarylamines and potential application of the reaction to transformations of furane into indole derivatives; (b)-Synthesis of novel oxazole derivatives and their application in intermolecular Diels-Alder reaction as a part of vitamine B-6 synthesis, and aminolytical ring expansion of oxazoles to pyrimidone derivatives; (c)-Unusual reactivity of 3-hydroxy-4-pyrones with aromatic amines leading to polyfunctional cyclopentenones and some other, up to now undefined compounds. Normal reaction to 3-hydroxy-4-pyridones will be exploited in preparation of new examples of chelating compounds; (d)-Synthesis and oxidation of some thionamides to diimidoyl disulfides; (e)-Preparation of vinilogous benzothyazoles, potentially useful as colourants; (f)-Synthesis of mesoionic compounds, like sydnones, and their use in modification and transformation of macrolide antibiotics erithromicine and beta-lactames in an effort to improve the antibiotic activity; (g)-Regiospecific synthesis of semibulvalenes containing trifluoromethyl and some basic groups tend towards new antidepresives and preparation of enantiomerically pure or enriched samples for pharmacological testing; (h)-Synthesis of new aryl and heteroaryl-divinylbenzenes (heteroaryl e.g. furan, thiophene, pyrrole, oxazole, benzofuran, naphthofuran, piridine) followed by their intra- and intermolecular photochemical reactions i.e. photocycloaddition, photodehydrocyclization, photoaddition, photorearrangement, taking care of substituent effects on the course of the photochemical reactions; (i)-Photodehydrocyclizations of distyrylfuranes and distyrylthiophenes; (j)-Photorearrangements and photocycloadditions of 4-pyrones and 4-pyridones.

COOPERATION - PROJECTS


  1. Name of project: 1-07-038 FOTOSINTEZA POLINUKLEARNIH HETEROCIKLIČKIH KINOLONA I FOTOSINTEZA AZIRINA
    Name of institution: Fakultet kemijskog inženjerstva i tehnologije
    City: 10000 - Zagreb, Croatia

  2. Name of project: 1-07-333 SINTEZA I STEREODINAMIČKA ISTRAŽIVANJA KIRALNIH I FARMAKOLOŠKI ZANIMLJIVIH SPOJEVA
    Name of institution: FAKULTET KEMIJSKOG INŽENJERSTVA I TEHNOLOGIJE
    City: 10000 - Zagreb, Croatia

  3. Name of project: Before 30.08.93. CHIRAL HETEROCYCLIC BIARYLS AND HELICENES
    Name of institution: GERMAN-CROATIAN BILATERAL COOPERATION IN CHEMISTRY (before 30.08.1993.)
    City: Juelich, Deutschland

COOPERATION - INSTITUTIONS


  1. Name of institution: Institut Rugjer Bošković
    Type of institution: State institute
    Type of cooperation: Joint publishing of scientific papers
    City: 10000 - Zagreb, Croatia

  2. Name of institution: Prirodoslovno-matematički fakultet
    Type of institution: University/Faculty
    Type of cooperation: Joint publishing of scientific papers
    City: 10000 - Zagreb, Croatia

  3. Name of institution: PLIVA - tvornica kemijskih, farmaceutskih, kozmetičkih i prehrambenih proizvoda
    Type of institution: Economical/Production
    Type of cooperation: Joint publishing of scientific papers
    City: 10000 - Zagreb, Croatia

  4. Name of institution: Tekstilno-tehnološki fakultet
    Type of institution: University/Faculty
    Type of cooperation: Joint publishing of scientific papers
    City: 10000 - Zagreb, Croatia

  5. Name of institution: Katolieke Universiteit Nijmegen
    Type of institution: University/Faculty
    Type of cooperation: Systematic exchange of information
    City: Nijmegen, Nizozemska

  6. Name of institution: Bowling Green State University
    Type of institution: University/Faculty
    Type of cooperation: Systematic exchange of information
    City: Bowling Green, USA
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