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

ABSTRACT: 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.

SUBMITTER: Rajeev N

PROVIDER: S-EPMC7034244 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Rajeev Narasimhamurthy N Swaroop Toreshettahally R TR Alrawashdeh Ahmad I AI Rahman Shofiur S Alodhayb Abdullah A Anil Seegehalli M SM Kiran Kuppalli R KR Chandra Georghiou Paris E PE Rangappa Kanchugarakoppal S KS Sadashiva Maralinganadoddi P MP

Beilstein journal of organic chemistry 20200203

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. ...[more]

PMID: 32117472

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