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Nader NoshiranZadeh

Ali Ramazani, Nader Noshiranzadeh, Alieh Ghamkhari, KatarzynaS´ lepokura and Tadeusz Lis
One-Pot Diastereoselective Synthesis of Densely Functionalized 2H Indeno[ 2,1-b]furans. Single-Crystal X-Ray Structure of Dimethyl 8,8a- Dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2H-indeno[2,1-b]furan- 2,3- dicarboxylate
Abstract


Highly reactive 1 : 1 intermediates were produced in the reaction of Ph 3P and dialkyl acetylenedicarboxylates¼dialkyl but-2-ynedioates). Protonation of these intermediates by alcohols (2,2,2-¼ prop-2-yn-1-ol), MeOH, benzyl alcohol, and allyl alcohol¼ prop-2-en-1-ol) led to vinyltriphenylphosphonium salts 4, which underwent a Michael addition5 ( corresponding densely functionalized 2 structures of the final products were confirmed by IR, spectrometry. The configuration of dimethyl 8,8a-dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2 2,1- establishing that the one-pot multicomponent condensation reaction was completely diastereoselective. Scheme). Wittig reaction of the stabilized phosphonium ylides with ninhydrin (6) led to theH-indeno[2,1-b]furans 10 in fairly good yields (Table 1). The1H- and 13C-NMR spectroscopy, and massH-indeno[b]furan-2,3-dicarboxylate (10a) was established by a single-crystal X-ray structure determination, ( trichloroethanol, propargyl alcohol ( ( reaction with the conjugate base to produce the corresponding stabilized phosphonium ylides

 

 

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