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

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...

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Autores principales: Rajeev, Narasimhamurthy, Swaroop, Toreshettahally R, Alrawashdeh, Ahmad I, Rahman, Shofiur, Alodhayb, Abdullah, Anil, Seegehalli M, Kiran, Kuppalli R, Chandra, Georghiou, Paris E, Rangappa, Kanchugarakoppal S, Sadashiva, Maralinganadoddi P
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7034244/
https://www.ncbi.nlm.nih.gov/pubmed/32117472
http://dx.doi.org/10.3762/bjoc.16.18
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author Rajeev, Narasimhamurthy
Swaroop, Toreshettahally R
Alrawashdeh, Ahmad I
Rahman, Shofiur
Alodhayb, Abdullah
Anil, Seegehalli M
Kiran, Kuppalli R
Chandra,
Georghiou, Paris E
Rangappa, Kanchugarakoppal S
Sadashiva, Maralinganadoddi P
author_facet Rajeev, Narasimhamurthy
Swaroop, Toreshettahally R
Alrawashdeh, Ahmad I
Rahman, Shofiur
Alodhayb, Abdullah
Anil, Seegehalli M
Kiran, Kuppalli R
Chandra,
Georghiou, Paris E
Rangappa, Kanchugarakoppal S
Sadashiva, Maralinganadoddi P
author_sort Rajeev, Narasimhamurthy
collection PubMed
description 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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spelling pubmed-70342442020-02-28 The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates Rajeev, Narasimhamurthy Swaroop, Toreshettahally R Alrawashdeh, Ahmad I Rahman, Shofiur Alodhayb, Abdullah Anil, Seegehalli M Kiran, Kuppalli R Chandra, Georghiou, Paris E Rangappa, Kanchugarakoppal S Sadashiva, Maralinganadoddi P Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2020-02-03 /pmc/articles/PMC7034244/ /pubmed/32117472 http://dx.doi.org/10.3762/bjoc.16.18 Text en Copyright © 2020, Rajeev et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Rajeev, Narasimhamurthy
Swaroop, Toreshettahally R
Alrawashdeh, Ahmad I
Rahman, Shofiur
Alodhayb, Abdullah
Anil, Seegehalli M
Kiran, Kuppalli R
Chandra,
Georghiou, Paris E
Rangappa, Kanchugarakoppal S
Sadashiva, Maralinganadoddi P
The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
title The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
title_full The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
title_fullStr The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
title_full_unstemmed The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
title_short The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
title_sort reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7034244/
https://www.ncbi.nlm.nih.gov/pubmed/32117472
http://dx.doi.org/10.3762/bjoc.16.18
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