Synthesis And Biological Activities Of New Triazole And Fused N-Heterocycles

As the rapid development of organic synthesis methodology over the last decades, many reactions with mild conditions, high atomic economy, easily accessible starting materials, versatle substrate and high yields have been developed, such as Ugi reaction, click reaction and Sonogashira reactions, which builds foundation for exploring compounds with new structure. In this dissertation, organic synthesis methodologies related to new pesticides were developed to synthesize compounds with new structure and high biological activities, especially fungicidal activities.There are two major parts separated by research approach in this paper. The first part is based on organic synthesis methodologies, which means proper synthetic strategies were chosen to synthesize fused heterocyclic compounds which are never been reported. And all the compounds were characterized and evaluated so that it could pave the way to looking for compounds with high biological activities, such as synthesis of 1H-pyrimido[2,1-b]quinazoline-2,6-diones via a Tandem aza-Wittig/nucleophilic addition/intramolecular cyclization/isomerization reaction(Chapter Ⅱ), synthesis of 2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine via intra-Ugi-3CC reaction (Chapter Ⅲ),5,6,7,8-tetrahydro-4H-[1,2,3]triazolo[1,5-a]azepin via sequential Ugi/alkyne-azide cycloaddition reactions(Chapter Ⅳ), synthesis of isoindolin-1-ones via sequential Ugi/Cyclization reaction(Chapter Ⅴ). The second part is mainly about design and synthesize new pesticides. First we summarized the commercialized pesticides, then we designed a new structure based on these pesticeides and synthesized them by using new organic synthesis methodologies. All the compounds were characterized and evaluated, such as the new type of compounds, 4,4-dimethyl-1-(1H-1,2,3-triazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)-pentan-3-ols, were synthesized in one-pot by using click reaction, and fungicidal activities results showed that some compounds exhibited signifacant activity superior to those of the agricultural fungicide Triadimefon(Chapter Ⅵ), the new type of compounds,2,2-dimethyl-7-aryl-4-(1H-1,2,4-triazol-1-yl)hept-6-yn-3-ols, were synthesized in one-pot by using Palladium-catalyzed reactions and fungicidal activities results showed that some compounds exhibited signifacant activity superior to those of the agricultural fungicide Diniconazole(Chapter Ⅶ). Details were summarized as follow:1.The latest development and applications of aza-Wittig reaction, Baylis-Hillman reaction and Ugi reaction in synthesis of heterocyclic compounds and the development of pesicides are reviewed.2. 1H-Pyrimido[2,1-b]quinazoline-2,6-diones are prepared, by using a new tandem aza-Wittig/nucleophilic addition/intramolecular cyclization/isomerization reaction starting from the Baylis-Hillman adducts. Due to the very simple operation of the synthetic approach, this synthetic method has the potential in preparation of various 1H-pyrimido[2,1-b]quinazoline-2,6-diones, which are of considerable interest as potential biological active compounds or pharmaceuticals.3. New efficient synthesis of 2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine by intra-Ugi-3CR was developed. Fifteen new compounds were synthesized with a simple and one-pot way, which are of considerable interest as potential biological active compounds or pharmaceuticals.4. A new efficient synthesis of 5,6,7,8-tetrahydro-4H-[1,2,3]triazolo[1,5-a]azepin by sequential Ugi/alkyne-azide cycloaddition reactions was developed. Twenty new compounds were synthesized with a simple and one-pot way, which are of considerable interest as potential biological active compounds or pharmaceuticals.5. A new efficient synthesis of isoindolin-1-ones via sequential Ugi-3CR/cyclization reaction was developed. The mild reaction conditions and the easy availability of starting materials make this method a valuable tool for generating isoindolin-1-ones, which are of considerable interest in biological and medicinal chemstry.6. The new type of compounds,4,4-dimethyl-1-(1H-1,2,3-triazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)-pentan-3-ols, were synthesized in one-pot by using click reaction and fungicidal activities results showed that some compounds exhibited signifacant activity superior to those of the agricultural fungicide Triadimefon. These compounds are very potential as lead compounds in pesticide. N37. A new type of compounds,2,2-dimethyl-7-aryl-4-(1H-1,2,4-triazol-1-yl)hept-6-yn-3-ols, were synthesized in one-pot by using Sonogashra reaction, and the fungicidal activities results showed that some compounds exhibited signifacant activity superior to those of the agricultural fungicide Diniconazole. These compounds are very potential as lead compounds in pesticide.