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Sustainable and scalable synthesis of polysubstituted bis-1,2,4-triazoles, bis-2-iminothiazolines and bis-thiobarbiturates using bis-N,N-disubstituted thioureas as versatile substrate.
R Soc Open Sci 2019; 6(6):181963RS

Abstract

An expedient and tandem regioselective one-pot protocol for the sono-synthesis of bis-[1,2,4]-triazol-3-yl amines and bis-2-iminothiazolines from corresponding bis-1,3-disubstituted thioureas has been developed. The products' regioselectivity correlate well with the pK as of the parent amines, in which the amine possessing higher pK a goes to the ring nitrogen, whereas the other nitrogen remains flanked as an exocyclic nitrogen of the bis-triazole or bis-thiazole moieties. Further, the sonochemical preparation of both bis-5-(2-nitrobenzylidene) thiobarbiturates and bis-2-thioxoimidazolidine-4,5-diones from bis-1,3-disubstituted thioureas has also been achieved. The obtained bis-5-(2-nitrobenzylidene)thiobarbiturates easily underwent reductive cyclization to afford the corresponding bis-5-benzo[c]isoxazol-3-ylidenethiobarbiturates. The scope and limitations of these strategies have been studied. Moreover, the suggested methodologies have advantages such as broad functional group tolerance, mild conditions, operational simplicity and applicability on a gram scale. Furthermore, the protocols scored well in a number of green metrics, subsequently showing these approaches to be environmentally benign and sustainable processes.

Authors+Show Affiliations

Department of Chemistry, College of Science, Jouf University, PO Box 2014, Sakaka, Aljouf, Kingdom of Saudi Arabia. Department of Chemistry, Faculty of Science, Fayoum University, PO Box 63514 Fayoum City, Egypt.Department of Chemistry, Faculty of Science, Fayoum University, PO Box 63514 Fayoum City, Egypt.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31312476

Citation

Arafa, Wael Abdelgayed Ahmed, and Hamada Mohamed Ibrahim. "Sustainable and Scalable Synthesis of Polysubstituted Bis-1,2,4-triazoles, Bis-2-iminothiazolines and Bis-thiobarbiturates Using bis-N,N-disubstituted Thioureas as Versatile Substrate." Royal Society Open Science, vol. 6, no. 6, 2019, p. 181963.
Arafa WAA, Ibrahim HM. Sustainable and scalable synthesis of polysubstituted bis-1,2,4-triazoles, bis-2-iminothiazolines and bis-thiobarbiturates using bis-N,N-disubstituted thioureas as versatile substrate. R Soc Open Sci. 2019;6(6):181963.
Arafa, W. A. A., & Ibrahim, H. M. (2019). Sustainable and scalable synthesis of polysubstituted bis-1,2,4-triazoles, bis-2-iminothiazolines and bis-thiobarbiturates using bis-N,N-disubstituted thioureas as versatile substrate. Royal Society Open Science, 6(6), p. 181963. doi:10.1098/rsos.181963.
Arafa WAA, Ibrahim HM. Sustainable and Scalable Synthesis of Polysubstituted Bis-1,2,4-triazoles, Bis-2-iminothiazolines and Bis-thiobarbiturates Using bis-N,N-disubstituted Thioureas as Versatile Substrate. R Soc Open Sci. 2019;6(6):181963. PubMed PMID: 31312476.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sustainable and scalable synthesis of polysubstituted bis-1,2,4-triazoles, bis-2-iminothiazolines and bis-thiobarbiturates using bis-N,N-disubstituted thioureas as versatile substrate. AU - Arafa,Wael Abdelgayed Ahmed, AU - Ibrahim,Hamada Mohamed, Y1 - 2019/06/19/ PY - 2018/11/20/received PY - 2019/05/22/accepted PY - 2019/7/18/entrez PY - 2019/7/18/pubmed PY - 2019/7/18/medline KW - bis-2-iminothiazolines KW - bis-[1,2,4]-triazol-3-yl amines KW - green metrics KW - regioselectivity KW - ultrasonic irradiation SP - 181963 EP - 181963 JF - Royal Society open science JO - R Soc Open Sci VL - 6 IS - 6 N2 - An expedient and tandem regioselective one-pot protocol for the sono-synthesis of bis-[1,2,4]-triazol-3-yl amines and bis-2-iminothiazolines from corresponding bis-1,3-disubstituted thioureas has been developed. The products' regioselectivity correlate well with the pK as of the parent amines, in which the amine possessing higher pK a goes to the ring nitrogen, whereas the other nitrogen remains flanked as an exocyclic nitrogen of the bis-triazole or bis-thiazole moieties. Further, the sonochemical preparation of both bis-5-(2-nitrobenzylidene) thiobarbiturates and bis-2-thioxoimidazolidine-4,5-diones from bis-1,3-disubstituted thioureas has also been achieved. The obtained bis-5-(2-nitrobenzylidene)thiobarbiturates easily underwent reductive cyclization to afford the corresponding bis-5-benzo[c]isoxazol-3-ylidenethiobarbiturates. The scope and limitations of these strategies have been studied. Moreover, the suggested methodologies have advantages such as broad functional group tolerance, mild conditions, operational simplicity and applicability on a gram scale. Furthermore, the protocols scored well in a number of green metrics, subsequently showing these approaches to be environmentally benign and sustainable processes. SN - 2054-5703 UR - https://www.unboundmedicine.com/medline/citation/31312476/Sustainable_and_scalable_synthesis_of_polysubstituted_bis-1,2,4-triazoles,_bis-2-iminothiazolines_and_bis-thiobarbiturates_using_bis-N,N-disubstituted_thioureas_as_versatile_substrate L2 - https://royalsocietypublishing.org/doi/full/10.1098/rsos.181963?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub=pubmed DB - PRIME DP - Unbound Medicine ER -