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1.
RSC Adv ; 9(17): 9468-9474, 2019 Mar 22.
Article in English | MEDLINE | ID: mdl-35520747

ABSTRACT

A carbonylative Sonogashira coupling approach to the synthesis of glyco-alkynones is described. Eighteen examples were obtained in moderate do nearly quantitative yields under mild conditions employing Mo(CO)6 as a safe carbon monoxide source. Functionalization of the alkynyl moiety via cycloaddition with organic azides provided six examples of glyco-triazoles.

2.
Adv Synth Catal, v. 361, n. 13, p. 3163-3172, apr. 2019
Article in English | Sec. Est. Saúde SP, SESSP-IBPROD, Sec. Est. Saúde SP | ID: bud-2838

ABSTRACT

The iron(III)-promoted synthesis of densely-substituted 4H-chalcogenchromene from organochalcogen propargylamines in the presence of diaryl dichalcogenides is reported. Subsequent C2-functionalization with electrophiles and potassium trifluoroborate salts via Suzuki-Miyaura coupling reaction are also presented. A plausible mechanism based on HRMS experiments is proposed and discussed.

3.
RSC Adv, v. 9, n. 17, p. 9468-9474, mar. 2019
Article in English | Sec. Est. Saúde SP, SESSP-IBPROD, Sec. Est. Saúde SP | ID: bud-2735

ABSTRACT

A carbonylative Sonogashira coupling approach to the synthesis of glyco-alkynones is described. Eighteen examples were obtained in moderate do nearly quantitative yields under mild conditions employing Mo(CO)6 as a safe carbon monoxide source. Functionalization of the alkynyl moiety via cycloaddition with organic azides provided six examples of glyco-triazoles.

4.
New J Chem, v. 43, n. 2, p. 696-699, jan. 2019
Article in English | Sec. Est. Saúde SP, SESSP-IBPROD, Sec. Est. Saúde SP | ID: bud-2642

ABSTRACT

The synthesis of amidoglucals and glucal esters in good to high yields using 2-iodo-3,4,6-tri-O-acetyl-d-glucal as a substrate, Mo(CO)(6) as a carbon monoxide source and PdCl2 as a catalyst is reported. This procedure shows advantages when compared to other published methodologies, as it is carried out in one pot relying on short reaction times at mild temperatures, under ligand-free conditions and with only one equivalent of Mo(CO)(6).

5.
Adv. synth. catal. ; 361(13): 3163-3172, 2019.
Article in English | Sec. Est. Saúde SP, SESSP-IBPROD, Sec. Est. Saúde SP | ID: but-ib17197

ABSTRACT

The iron(III)-promoted synthesis of densely-substituted 4H-chalcogenchromene from organochalcogen propargylamines in the presence of diaryl dichalcogenides is reported. Subsequent C2-functionalization with electrophiles and potassium trifluoroborate salts via Suzuki-Miyaura coupling reaction are also presented. A plausible mechanism based on HRMS experiments is proposed and discussed.

6.
RSC Adv ; 9(17): 9468-9474, 2019.
Article in English | Sec. Est. Saúde SP, SESSP-IBPROD, Sec. Est. Saúde SP | ID: but-ib15969

ABSTRACT

A carbonylative Sonogashira coupling approach to the synthesis of glyco-alkynones is described. Eighteen examples were obtained in moderate do nearly quantitative yields under mild conditions employing Mo(CO)6 as a safe carbon monoxide source. Functionalization of the alkynyl moiety via cycloaddition with organic azides provided six examples of glyco-triazoles.

7.
New J Chem ; 43(2): 696-699, 2019.
Article in English | Sec. Est. Saúde SP, SESSP-IBPROD, Sec. Est. Saúde SP | ID: but-ib15769

ABSTRACT

The synthesis of amidoglucals and glucal esters in good to high yields using 2-iodo-3,4,6-tri-O-acetyl-d-glucal as a substrate, Mo(CO)(6) as a carbon monoxide source and PdCl2 as a catalyst is reported. This procedure shows advantages when compared to other published methodologies, as it is carried out in one pot relying on short reaction times at mild temperatures, under ligand-free conditions and with only one equivalent of Mo(CO)(6).

8.
ACS Omega ; 3(6): 6476-6482, 2018 Jun 30.
Article in English | MEDLINE | ID: mdl-30023949

ABSTRACT

Three tobacco types (Burley, Flue Cured, and Oriental) and eight cigarette brands were unequivocally identified using an electronic nose formed by only three sensors based on a single novel conducting polymer (PF-BTB) doped with different porphyrins (H2TPP, H2TPFP, and H2BTBOP). The synthesis and characterization of the polymer are also discussed. Small changes in the porphyrin structure caused significant changes in the electrical conductance response patterns of the sensors upon exposure to complex chemical matrixes, representing a novel approach for tuning the selectivity of chemiresistive sensors for e-nose application. This e-nose is fast, cheap, reliable, can be easily operated, and could be a valuable tool for border agents fighting cigarette smuggling around the world, helping them prevent losses of millions in tax revenues and sales.

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