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صفحه اصلی
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بیست و نهمین کنفرانس شیمی آلی ایران
The new synthesis of pyrrole-fused dibenzo[b,f][1,4]oxazepine/thiazepines by the pseudo-Joullié-Ugi reaction via an unexpected route with high chemoselectivity
نویسندگان :
Mohammad Taghi Nazeri ( دانشگاه شهید بهشتی ) , Masoomeh Ahmadi ( دانشگاه شهید بهشتی ) , Maryam Ghasemi ( دانشگاه شهید بهشتی ) , Ahmad Shaabani ( دانشگاه شهید بهشتی ) , Behrouz Notas ( دانشگاه شهید بهشتی )
کلید واژه ها :
Joullié-Ugi reaction،Cyclic imine،Dibenzoxazepine،Pyrrole،Isocyanide،Acetylenedicarboxylate
چکیده مقاله :
In this paper, we designed a new and unexpected route for the synthesis of pyrrole-fused dibenzoxazepines/thiazepines based on the modified Ugi reaction of cyclic imines with isocyanides and acetylenedicarboxylates under catalyst-free conditions. Mechanism investigation indicates that this process is carried out through the production of zwitterion species (Huisgen’s 1,4-dipole), which is a key intermediate in the chemo selectivity of products. This Huisgen’s 1,4-dipole is trapped in situ with isocyanides, and various pyrrole-fused dibenzoxazepines/thiazepines are synthesized in a simple one-pot operation with high yields and chemoselectivity. This strategy opens a new route in Ugi reactions (pseudo-Joullié-Ugi reaction) for synthesizing pyrrole-fused heterocycles as unique pharmaceutical scaffolds. This efficient, simple and catalyst-free method can be successfully performed in gram-scale reactions. In addition, the new approach is repeatable for other cyclic imines. Interestingly, the pyrrole-fused dibenzoxazepines/thiazepine derivative has remarkable emission, which could be a potential candidate for optoelectronic conjugated materials.
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