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Javanbani, Hamideh, Ramazani, Ali, Joo, Sang Woo, Ahmadi, Yavar, Azizkhani, Vahid, Azimzadeh Asiabi, Pegah. (1394). Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines. فصلنامه علمی زیست فناوری گیاهان زراعی, 3(Issue 4, pp. 283-387, Serial No. 9), 310-322.
Hamideh Javanbani; Ali Ramazani; Sang Woo Joo; Yavar Ahmadi; Vahid Azizkhani; Pegah Azimzadeh Asiabi. "Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines". فصلنامه علمی زیست فناوری گیاهان زراعی, 3, Issue 4, pp. 283-387, Serial No. 9, 1394, 310-322.
Javanbani, Hamideh, Ramazani, Ali, Joo, Sang Woo, Ahmadi, Yavar, Azizkhani, Vahid, Azimzadeh Asiabi, Pegah. (1394). 'Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines', فصلنامه علمی زیست فناوری گیاهان زراعی, 3(Issue 4, pp. 283-387, Serial No. 9), pp. 310-322.
Javanbani, Hamideh, Ramazani, Ali, Joo, Sang Woo, Ahmadi, Yavar, Azizkhani, Vahid, Azimzadeh Asiabi, Pegah. Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines. فصلنامه علمی زیست فناوری گیاهان زراعی, 1394; 3(Issue 4, pp. 283-387, Serial No. 9): 310-322.

Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines

Iranian chemical communication
مقاله 4، دوره 3، Issue 4, pp. 283-387, Serial No. 9، دی 2015، صفحه 310-322    اصل مقاله (392.25 K)
نوع مقاله: Original Research Article
نویسندگان
Hamideh Javanbani1؛ Ali Ramazani* 2؛ Sang Woo Joo3؛ Yavar Ahmadi4؛ Vahid Azizkhani5؛ Pegah Azimzadeh Asiabi6
1University of Zanjan
2UNIVERSITY OF ZANJAN
3Yeungnam University
4Young Researchers and Elite Clube, Marand Branch, Islamic Azad University
5Payame Noor University
6Nuclear Science and Technology Research Institute
چکیده
Reactions of N-isocyaniminotriphenylphosphorane with cyclopentanone have been studied in the presence of aromatic carboxylic acids and primary amines, proceeds smoothly at room temperature under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives by an intramolecular Aza-Wittig cyclization in CH2Cl2 in excellent yields. The structures of the products were deduced from their IR, Mass, ¹H NMR, and ¹³C NMR spectra. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed. The method offers a mild, simple, and efficient route for the preparation of fully substituted 1,3,4-oxadiazoles from cyclopentanone, primary amines, N-isocyaniminotriphenylphosphorane and aromatic carboxylic acids. Easy work-up, high yields and fairly mild reaction conditions make it a useful procedure in comparison to the modern synthetic methodologies.
کلیدواژه‌ها
N-isocyaniminotriphenylphosphorane؛ cyclopentanone؛ aromatic carboxylic acids؛ primary amines؛ oxadiazole
مراجع
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