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1.
RSC Adv ; 14(22): 15597-15603, 2024 May 10.
Article in English | MEDLINE | ID: mdl-38746844

ABSTRACT

A highly efficient method for the direct construction of amide bonds via a selective cleavage of C-H and C[double bond, length as m-dash]C bonds in indole structures using an iodine-promoted approach was developed. Mechanistic studies indicated the formation of superoxide radicals obtained from molecular oxygen activation as a key intermediate step, which provided a precursor for subsequent oxidative ring-opening and intermolecular cyclization. A broad range of quinazolin-4(3H)-ones and tryptanthrins were synthesized in moderate to good yields under mild and environmentally benign conditions.

2.
RSC Adv ; 10(72): 44332-44338, 2020 Dec 09.
Article in English | MEDLINE | ID: mdl-35517165

ABSTRACT

A novel synthesis of furocoumarins was developed by a reaction between oxime esters and 4-hydroxycoumarins. The reaction was proposed to undergo radical mechanism mediated by iodine, a cheap and common laboratory reagent. Mechanistic studies showed the key for the successful transformation was the presence of α-iodoimine intermediate which facilitated the ring-closing step. The developed conditions produced good functional group tolerance with a wide range of high-profile furocoumarin product. The potential for this strategy to be applied in other syntheses of heterocyclic compounds is highly achievable.

3.
RSC Adv ; 8(55): 31455-31464, 2018 Sep 05.
Article in English | MEDLINE | ID: mdl-35548194

ABSTRACT

A Cu2(OBA)2(BPY) metal-organic framework was utilized as a productive heterogeneous catalyst for the synthesis of 3-aroylquinolines via one-pot domino reactions of 2-aminobenzylalcohols with propiophenones. This Cu-MOF was considerably more active towards the one-pot domino reaction than a series of transition metal salts, as well as nano oxide and MOF-based catalysts. The MOF-based catalyst was reusable without a significant decline in catalytic efficiency. To the best of our knowledge, the transformation of 2-aminobenzylalcohols to 3-aroylquinolines was not previously reported in the literature, and this protocol would be complementary to previous strategies for the synthesis of these valuable heterocycles.

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