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Taghizadeh, Mohammad Javad, Jadidi, Khosrow. (1393). A novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides. فصلنامه علمی زیست فناوری گیاهان زراعی, 3(Issue 1, pp. 1-71, Serial No.6), 57-61.
Mohammad Javad Taghizadeh; Khosrow Jadidi. "A novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides". فصلنامه علمی زیست فناوری گیاهان زراعی, 3, Issue 1, pp. 1-71, Serial No.6, 1393, 57-61.
Taghizadeh, Mohammad Javad, Jadidi, Khosrow. (1393). 'A novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides', فصلنامه علمی زیست فناوری گیاهان زراعی, 3(Issue 1, pp. 1-71, Serial No.6), pp. 57-61.
Taghizadeh, Mohammad Javad, Jadidi, Khosrow. A novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides. فصلنامه علمی زیست فناوری گیاهان زراعی, 1393; 3(Issue 1, pp. 1-71, Serial No.6): 57-61.

A novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides

Iranian chemical communication
مقاله 7، دوره 3، Issue 1, pp. 1-71, Serial No.6، فروردین 2015، صفحه 57-61    اصل مقاله (867.69 K)
نوع مقاله: Short communication
نویسندگان
Mohammad Javad Taghizadeh* 1؛ Khosrow Jadidi2
1Department of Chemistry, Imam Hossein University, PB BOX 995-16765 Tehran, Iran
2Department of Chemistry, Shahid Beheshti University, PB BOX 1983963113 Tehran, Iran
چکیده
An efficient one-pot three-component procedure for the synthesis of new chiral spiro oxindolopyrrolidines/pyrrolizidines with highly regio- and diastereo-enantio, selective from 1,3-dipolar cycloaddition of azomethine ylides and chiral menthol-drived trans-cinnamic are described. The mechanism of the reaction is discussed on basis of the assignment of the absolute configuration of one of the cycloaddition products, which obtained by single crystal X-ray analysis. The process occurs at reflux temperature in ethanol as green solvent and in the absence of any bidentate chelating Lewis acids. Functionalized pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds.1 Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems.
کلیدواژه‌ها
Chiral spiro oxindolopyrrolidines؛ pyrrolizidines؛ azomethine ylides؛ chiral menthol-drived trans-cinnamic؛ isatin؛ sarcosine
مراجع
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[9] A.K. Ganguly, N. Seah, V. Popov, C.H. Wang, R. Kuang, A.K. Saksena, B.N. Pramanik, T.M. Chan, A.T. McPhail, Tetrahedron Lett., 2002, 43, 8981-9883.

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