2,6-Dicyano-4-pyrone as a Novel and Multifarious Building Block for the Synthesis of 2,6-Bis(hetaryl)-4-pyrones and 2,6-Bis(hetaryl)-4-pyridinols.
Journal
ACS omega
ISSN: 2470-1343
Titre abrégé: ACS Omega
Pays: United States
ID NLM: 101691658
Informations de publication
Date de publication:
29 Dec 2020
29 Dec 2020
Historique:
received:
03
11
2020
accepted:
02
12
2020
entrez:
6
1
2021
pubmed:
7
1
2021
medline:
7
1
2021
Statut:
epublish
Résumé
In this work, a three-stage and easily scalable synthesis of 2,6-dicyano-4-pyrone (overall yield of 45%) as a new convenient building block has been developed from diethyl acetonedioxalate. It was shown that the transformation with hydroxylamine and [3 + 2]-cycloaddition, in contrast to the reactions with hydrazines, selectively proceed through the attack at the cyano groups without the pyrone ring-opening to give symmetrical and unsymmetrical pyrone-bearing heterocyclic triads containing 1,2,4- and 1,3,4-oxadiazoles as well as tetrazole moieties. The reaction of 2,6-bis(hetaryl)-4-pyrones with ammonia afforded 2,6-bis(hetaryl)pyridines in 63-87% yields. The 4-pyridone/4-pyridinol tautomerism of 2,6-bis(hetaryl)pyridinols and the influence of the nature of adjacent azolyl moieties on this equilibrium have been discussed.
Identifiants
pubmed: 33403303
doi: 10.1021/acsomega.0c05357
pmc: PMC7774280
doi:
Types de publication
Journal Article
Langues
eng
Pagination
33406-33420Informations de copyright
© 2020 The Authors. Published by American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
Références
Chemistry. 2017 Feb 3;23(8):1965-1971
pubmed: 27911484
Angew Chem Int Ed Engl. 2015 Jan 12;54(3):786-91
pubmed: 25521940
Chemistry. 2020 Jan 7;26(2):428-437
pubmed: 31489718
J Org Chem. 2018 Feb 16;83(4):1898-1902
pubmed: 29368516
J Med Chem. 2018 Dec 13;61(23):10502-10518
pubmed: 30457335
ACS Nano. 2017 Sep 26;11(9):9162-9175
pubmed: 28836765
Chem Asian J. 2015 May;10(5):1098-115
pubmed: 25630960
Angew Chem Int Ed Engl. 2013 Dec 2;52(49):13071-5
pubmed: 24123891
Angew Chem Int Ed Engl. 2012 Jun 4;51(23):5642-6
pubmed: 22532445
Org Biomol Chem. 2018 Mar 7;16(10):1692-1707
pubmed: 29451283
Inorg Chem. 2019 Nov 4;58(21):14642-14651
pubmed: 31609595
Chemistry. 2012 Nov 5;18(45):14487-96
pubmed: 22996572
J Org Chem. 2017 Jul 21;82(14):7085-7092
pubmed: 28682073
Molecules. 2018 Aug 28;23(9):
pubmed: 30154319
J Org Chem. 2016 Dec 16;81(24):12532-12539
pubmed: 27978717
Chem Commun (Camb). 2014 Sep 14;50(71):10323-6
pubmed: 25058142
Chem Commun (Camb). 2013 Dec 4;49(93):10986-8
pubmed: 24136154
Chemistry. 2007;13(35):9834-40
pubmed: 17948330
Inorg Chem. 2016 Apr 4;55(7):3685-91
pubmed: 26991111
Chemistry. 2016 Dec 12;22(50):17892-17908
pubmed: 27515469
J Am Chem Soc. 2016 Apr 13;138(14):4722-5
pubmed: 27015009
J Am Chem Soc. 2018 Feb 14;140(6):2355-2362
pubmed: 29357236
Dalton Trans. 2018 Nov 13;47(44):15725-15736
pubmed: 30334556
Chemistry. 2013 Dec 9;19(50):17141-9
pubmed: 24307370
Chem Soc Rev. 2014 Aug 7;43(15):5302-25
pubmed: 24871484
Dalton Trans. 2015 Sep 21;44(35):15611-9
pubmed: 26245980
J Am Chem Soc. 2019 Jul 17;141(28):11204-11211
pubmed: 31274293
Angew Chem Int Ed Engl. 2007;46(21):3926-30
pubmed: 17427165
Inorg Chem. 2018 May 7;57(9):5096-5107
pubmed: 29688008
J Org Chem. 2019 Mar 15;84(6):3524-3536
pubmed: 30810032
Nat Chem. 2016 Jan;8(1):10-5
pubmed: 26673259
Chemistry. 2012 Jun 4;18(23):7269-77
pubmed: 22517539
J Org Chem. 2019 Nov 15;84(22):14558-14570
pubmed: 31647644
J Am Chem Soc. 2017 Oct 18;139(41):14605-14610
pubmed: 28914532
Chem Pharm Bull (Tokyo). 1982 Dec;30(12):4314-24
pubmed: 7168865
Chem Commun (Camb). 2017 Oct 18;53(81):11217-11220
pubmed: 28956560
Dalton Trans. 2020 Jan 28;49(4):1022-1031
pubmed: 31859300
Org Lett. 2008 Mar 20;10(6):1151-4
pubmed: 18303898
Angew Chem Int Ed Engl. 2011 Sep 5;50(37):8745-9
pubmed: 21812083
Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22
pubmed: 18156677
Chem Sci. 2016 Mar 1;7(3):1653-1673
pubmed: 30155012
Chemistry. 2006 Oct 10;12(29):7733-41
pubmed: 16871503
Dalton Trans. 2020 Jun 14;49(22):7496-7506
pubmed: 32441717
Chem Rev. 2019 Jan 23;119(2):1323-1455
pubmed: 30192523