Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

Shang, Zhi‐Hao; Sun, Jina; Guo, Jiang-Shan; Sun, Yuanyuan; Weng, Weijun; Zhang, Zhen-Xiao; Li, Zeng-Jing; Zhu, Yan‐Ping

doi:10.1016/j.tet.2019.130887

Cited by 13 publications

(5 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Another successful example was shown by Shang and group, used benzohydrazides and methyl-azaheteroarenes derivatives in combination with iodine and DMSO, supported by the use of base K 2 CO 3 (Scheme 52 (k)). [524] The whole process has been found to be having a broad substrate scope and appreciable yields of up to 74 %.…”

Section: Csp 3 à O Bond Formationmentioning

confidence: 96%

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Reetu,

Kalita,

Dash

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis of the use of iodine and DMSO in various synthetic routes for the preparation of valuable targets are presented. These methods reduce the acceptance on expensive additives and reagents, and offer a more sustainable solution for the synthesis of these important chemical scaffolds.

show abstract

Section: Csp 3 à O Bond Formationmentioning

confidence: 96%

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Reetu,

Kalita,

Dash

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…Synthesis of the same scaffold was next reported by Shang and Zhu et al in 2020 (Scheme 30). 47 Reaction of 2/4-methyl pyridines 21/22 or 2/4-methyl quinolines 25/26 or 2-methyl quinoxaline 29 or 2-methyl-1,8-naphthyridines 28 with hydrazides 122 in the presence of 2.5 equivalents of iodine and 5 equivalents of K 2 CO 3 as a base at 110 °C in the DMSO medium resulted in the formation of azaarene linked oxadiazoles 123 . In the optimization study, the authors screened several bases such as K 2 CO 3 , Na 2 CO 3 , Cs 2 CO 3 , NaHCO 3 , KH 2 PO 4 , K 3 PO 4 and NaOH.…”

Section: Kornblum Oxidationmentioning

confidence: 99%

Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

Acharya,

Patra,

Barad

et al. 2024

New J. Chem.

View full text Add to dashboard Cite

show abstract

“…In 2013, Chang and co-workers reported an oxidative annulation of aryl carbaldehydes with alkyl- and benzohydrazides with two heteroaryl carbaldehyde examples . Contemporary strategies combining methyl-heteroarene oxidation and subsequent 1,3,4-oxadiazole formation via independent disclosures by Kamal and Zhu have also been reported . Huang has published the utility of sp 2 - and sp -functionalized arenes for cyclization with benzohydrazides .…”

Section: Introductionmentioning

confidence: 99%

“…12 Contemporary strategies combining methyl-heteroarene oxidation and subsequent 1,3,4-oxadiazole formation via independent disclosures by Kamal 13 reported. 14 Huang has published the utility of sp 2 -and spfunctionalized arenes for cyclization with benzohydrazides. 15 The use of alternative oxidative cyclization approaches incorporating iodine, 16 hypervalent iodine reagents, 17 in addition to environmentally benign oxidants, have also been disseminated.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthetic Access to Unsymmetric, Tridentate, Pyridyl-1,3,4-oxadiazole Complexants via Intramolecular Oxidative Annulation of Arylhydrazides with Heteroaryl Carbaldehydes

Dzeagu

Carrick

2022

J. Org. Chem.

View full text Add to dashboard Cite

Over the last four decades, an ideal complexant for the chemoselective liquid−liquid separation of the minor actinides from the lanthanides contained within spent nuclear fuel has yet to be realized. As strategic performance objectives continue to evolve as a function of time, solubility in process-relevant diluents, fast complexation kinetics, as well as robustness to hydro-and radiolytic degradation remain at the forefront of this grand challenge. While the vast majority of soft-N-donors are symmetric in nature, this laboratory has focused on defining synthetic methods to afford unsymmetric complexants for further study to explore the impact subtle changes to the molecular topography of the complexant moiety have on performance, in addition to working toward the definition of structure−activity relationships. The development of an intramolecular iodine-mediated oxidative annulation of heteroaryl-aryl-hydrazones for the production of functionalized, tridentate, and unsymmetric 1,3,4-oxadiazole-based complexants is reported. Optimization of reaction conditions afforded numerous products in high isolated yield over two linear steps in one pot in one hour of reaction time. The cleanliness of the optimized conditions negated the need for the chromatographic purification of 32 of 44 examples attempted. Method development, optimization, substrate scope, application to related heteroarenes, and a scale-up reaction are described herein.

show abstract

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

Cited by 13 publications

References 64 publications

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation

Synthetic Access to Unsymmetric, Tridentate, Pyridyl-1,3,4-oxadiazole Complexants via Intramolecular Oxidative Annulation of Arylhydrazides with Heteroaryl Carbaldehydes

Contact Info

Product

Resources

About

Facile synthesis of 1,3,4-oxadiazoles via iodine promoted oxidative annulation of methyl-azaheteroarenes and hydrazides

Cited by 13 publications

References 64 publications

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Recent advances in iodine–DMSO mediated C(sp3)–H functionalization of methyl-azaarenes via Kornblum oxidation

Synthetic Access to Unsymmetric, Tridentate, Pyridyl-1,3,4-oxadiazole Complexants via Intramolecular Oxidative Annulation of Arylhydrazides with Heteroaryl Carbaldehydes

Contact Info

Product

Resources

About

Recent advances in iodine–DMSO mediated C(sp³)–H functionalization of methyl-azaarenes via Kornblum oxidation