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1.
J Org Chem ; 89(7): 4628-4646, 2024 Apr 05.
Article in English | MEDLINE | ID: mdl-38497561

ABSTRACT

Primary and secondary alcohols have been converted into 2-amino-1,3-thiazoles under microwave irradiation, employing trichloroisocyanuric acid (TCCA) as a dual oxidant and chlorine source, TEMPO as a co-oxidant, and thiourea. Secondary alcohols underwent a single-stage, one-pot conversion process, while primary alcohols required a two-stage, one-pot procedure. Both transformations were completed within minutes (25-45 min). The versatility of this protocol extends to the synthesis of other heterocycles, including 1,3-selenazoles, 2-aminoimidazoles, imidazo[1,2-a]pyridines, quinoxalines, and hydrazino thiazoles by replacing thiourea with the appropriate surrogates.

2.
Org Biomol Chem ; 21(3): 590-599, 2023 01 18.
Article in English | MEDLINE | ID: mdl-36545812

ABSTRACT

A copper-iron-based catalyst has been prepared by a low-temperature co-precipitation and sonication method. The use of high-energy ultrasound reduces the time required for the preparation process from one workweek to one day with respect to the catalysts obtained by conventional coprecipitation and thermal treatment methods. The resulting material has been characterized at compositional, textural, structural, and chemical levels by ICP-AES, BET, SEM-EDS, XRD, TEM, and FTIR among other techniques. The material shows catalytic activity in the acyloxylation reaction of 1,4-dioxane and cyclohexene under microwave irradiation. In parallel with the optimized catalyst synthesis, the use of microwaves allowed for a substantial improvement in the outcome of the reaction in terms of cleanliness, yield, and time.


Subject(s)
Copper , Iron , Copper/chemistry , Microwaves , Cyclohexenes
3.
J Org Chem ; 86(23): 16409-16424, 2021 12 03.
Article in English | MEDLINE | ID: mdl-34709823

ABSTRACT

Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)4]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding ß-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.


Subject(s)
Alkynes , Phosphites , Catalysis , Copper , Cyclization , Microwaves , tert-Butylhydroperoxide
4.
J Org Chem ; 85(9): 6027-6043, 2020 May 01.
Article in English | MEDLINE | ID: mdl-32270681

ABSTRACT

The oxidative coupling of carboxylic acids with liquid ketones and cyclic ethers has been accomplished in minutes using t-butyl hydroperoxide in the presence of tetrabutylammonium iodide under microwave irradiation in the absence of a solvent. In addition to drastically shortening the reaction times, the use of microwaves resulted, in general, in yields equal to or higher than those obtained by conventional heating.

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