A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides

Kumar, K.S. Vinay; Swaroop, Toreshettahally R.; Rajeev, Narasimhamurthy; Vinayaka, A. C.; Lingaraju, Gejjalagere S.; Rangappa, Kanchugarakoppal S.; Sadashiva, M. P.

doi:10.1055/s-0035-1561391

Cited by 13 publications

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References 40 publications

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“…As a part of our work on the development of new synthetic methods [26][27][28][29][30], we have recently reported the synthesis of thiazoles from xanthate esters [31]. In continuation of this ongoing work, we planned to synthesize 5-alkoxy-4-arylthiazoles 3 by the sodium hydride/DMF-mediated reaction of arylmethyl isocyanides 2 with S-alkyl xanthate esters 1 or O-aryl/Oalkyl dithiocarbonates.…”

Section: Introductionmentioning

confidence: 99%

The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

Rajeev

Swaroop

Alrawashdeh

et al. 2020

Beilstein J. Org. Chem.

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An unexpected formation of carbamothioates by a sodium hydride-mediated reaction of arylmethyl isocyanides with xanthate esters in DMF is reported. The products thus obtained were compared with the carbamothioates obtained by the sodium hydride-mediated condensation of the corresponding benzylamines and xanthate esters in DMF. To account for these unexpected reactions, a mechanism is proposed in which the key steps are supported by quantum chemical calculations.

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Section: Introductionmentioning

confidence: 99%

The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

Rajeev

Swaroop

Alrawashdeh

et al. 2020

Beilstein J. Org. Chem.

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Reaction Conditions for the Regiodivergent Direct Arylations at C2‐ or C5‐Positions of Oxazoles using Phosphine‐Free Palladium Catalysts

2019

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Two sets of reaction conditions for the regiodivergent C2-or C5-direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2-or C5-arylated oxazoles, a second palladium-catalyzed direct C-H bond arylation affords 2,5diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C-H bond functionalization steps. The Ru-catalyzed C-H arylation of the aryl unit of 2-aryloxazoles is also described.

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ChemInform Abstract: A One‐Pot Tandem Approach for the Synthesis of 5‐(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides.

et al. 2016

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A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides

Cited by 13 publications

References 40 publications

The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

Reaction Conditions for the Regiodivergent Direct Arylations at C2‐ or C5‐Positions of Oxazoles using Phosphine‐Free Palladium Catalysts

ChemInform Abstract: A One‐Pot Tandem Approach for the Synthesis of 5‐(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides.

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