Experimental and theoretical approaches to [1,5]-prototropic generation of an azomethine ylide and a 1,3-dipolar cycloaddition for novel spiropyrrolidine oxindoles synthesis
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作者:
Sarrafi, Yaghoub
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Univ Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, IranUniv Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, Iran
Sarrafi, Yaghoub
[1
]
Hamzehloueian, Mahshid
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Univ Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, IranUniv Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, Iran
Hamzehloueian, Mahshid
[1
]
Alimohammadi, Kamal
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Univ Payambare Aazam, Sari, IranUniv Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, Iran
Alimohammadi, Kamal
[2
]
Yeganegi, Saeid
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Univ Mazandaran, Fac Chem, Dept Phys Chem, Babol Sar 47416, IranUniv Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, Iran
Yeganegi, Saeid
[3
]
机构:
[1] Univ Mazandaran, Fac Chem, Dept Organ Chem, Babol Sar 47416, Iran
[2] Univ Payambare Aazam, Sari, Iran
[3] Univ Mazandaran, Fac Chem, Dept Phys Chem, Babol Sar 47416, Iran
A series of spiropyrrolidine oxindoles was synthesized via a multicomponent 1,3-dipolar cycloaddition reaction of isatin, benzylamine and chalcone derivatives. The regio- and stereochemistry of the products were established by single crystal X-ray structure and spectroscopic techniques. The molecular mechanism of this cycloaddition has been investigated by means of a density functional theory (OFT) method. The energy path in preparing the azomethine ylide via a [1.5]-H shift in an iminium ion was evaluated. The regio- and stereoselectivity were explained on the basis of transition states stabilities, global and local reactivity indices of the reactants. The cycloaddition has been assumed to take place through one-step pathway in which two C-C bonds are formed in a nonsynchronous way. (C) 2012 Elsevier B.V. All rights reserved.
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Univ Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, IndiaUniv Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, India
Acharjee, Nivedita
Banerji, Avijit
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Univ Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, IndiaUniv Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, India
Banerji, Avijit
Prange, Thierry
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Univ Paris 05, Lab Cristallog & RMN Biol, UMR 8015, CNRS, F-75006 Paris, FranceUniv Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, India
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Univ Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, IndiaUniv Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, India
Acharjee, Nivedita
Banerji, Avijit
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Univ Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, IndiaUniv Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, India
Banerji, Avijit
Prange, Thierry
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h-index: 0
机构:
Univ Paris 05, Lab Cristallog & RMN Biol, UMR 8015, CNRS, F-75006 Paris, FranceUniv Calcutta, Ctr Adv Studies Nat Prod Including Organ Synth, Dept Chem, Kolkata 700009, W Bengal, India