Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazine and 1,3,4-Thiadiazine from Substituted Acetophenones and Acid Hydrazides Using [Hydroxyl(tosyloxy)iodo]benzene

Karade, Nandkishor N.; Kondre, Jeevan M.; Gampawar, Sumeet V.; Shinde, Sandeep V.

doi:10.1080/00397910802654716

Cited by 9 publications

(3 citation statements)

References 8 publications

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“…Reaction of acetophenone with [hydroxyl(tosyloxy)iodo]benzene (HTIB) formed 470 , which on condensation with benzoic acid hydrazides afforded the acid hydrazones 471 which underwent requisite cyclization on addition of K 2 CO 3 to yield 2,5-diphenyl-6 H -1,3,4-oxadiazine 472 in 58–71% yields (Scheme ) …”

Section: Reactions Of Acid Hydrazidesmentioning

confidence: 99%

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

et al. 2014

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Section: Reactions Of Acid Hydrazidesmentioning

confidence: 99%

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

et al. 2014

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“…The same approach was effectively extended to synthesize 5‐aryl‐6H‐1,3,4‐thiadiazin‐2‐amine 100 through the HTIB mediated treatment of various enolizable ketones 3 with thiosemicarbazide 99 (Scheme 34). [75] …”

Section: Synthesis Of Heterocyclic Compounds Via Tosyloxylation Of Ketonesmentioning

confidence: 99%

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

et al. 2022

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Organo hypervalent iodine reagents are nowadays more attractive and versatile reagents for various chemical transformations in synthetic organic chemistry. These reagents are milder and having similar reactivity compared with toxic heavy metal reagents. Organo hypervalent iodine (λ3) reagents are successfully utilized to prepare synthetically and biologically important heterocycles. Hydroxy(tosyloxy)iodobenzene (HTIB) also acknowledged as Koser's reagent uses as an environmentally sustainable alternative to toxic heavy metals for the numerous and valuable organic transformations. The goal of this review is to highlight the recent advancements of the HTIB especially in the construction of heterocycles with various substitution patterns in a well‐organized form via tosyloxylation of ketones and oxidative cyclization methodology. This review compiles the up‐to‐date synthetic advancements of HTIB in the field of heterocycles.

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“…Karade et al . reported on the synthesis of 1,3,4‐oxadiazines from the reactions of [hydroxy(tosyloxy)iodo]benzene with substituted acetophenones, followed by the treatment with acid hydrazide and K 2 CO 3 . In another study, an efficient DMAP‐catalyzed [2 + 4] cycloaddition of allenoates and N ‐acyldiazenes was reported as a direct method for the synthesis of 1,3,4‐oxadiazine derivatives in moderate to good yields .…”

Section: Introductionmentioning

confidence: 99%

Unexpected Synthesis of 1,3,4‐Oxadiazines using extraordinary effect of SBA‐Pr‐SO₃H as the Nano–catalyst

et al. 2017

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Unexpected synthesis of 1,3,4‐oxadiazines has been accomplished through three‐component reaction of cyclohexyl isocyanide, hydrazide derivatives and cyclic ketones in the presence of a catalytic amount of SBA−Pr‐SO3H as an efficient catalyst. A range of spirooxadiazine derivatives were synthesized in high yields in a concise way. The same three‐component reaction in the presence of other acidic catalysts led to the synthesis of hydrazino amides. The formation of 1,3,4‐oxadiazines is related to the pore size and structure of SBA−Pr‐SO3H which spatial orientation of intermediate onto it leads to the formation of the oxadiazine ring.

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Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazine and 1,3,4-Thiadiazine from Substituted Acetophenones and Acid Hydrazides Using [Hydroxyl(tosyloxy)iodo]benzene

Cited by 9 publications

References 8 publications

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

Unexpected Synthesis of 1,3,4‐Oxadiazines using extraordinary effect of SBA‐Pr‐SO₃H as the Nano–catalyst

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Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazine and 1,3,4-Thiadiazine from Substituted Acetophenones and Acid Hydrazides Using [Hydroxyl(tosyloxy)iodo]benzene

Cited by 9 publications

References 8 publications

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

Unexpected Synthesis of 1,3,4‐Oxadiazines using extraordinary effect of SBA‐Pr‐SO3H as the Nano–catalyst

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Product

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About

Unexpected Synthesis of 1,3,4‐Oxadiazines using extraordinary effect of SBA‐Pr‐SO₃H as the Nano–catalyst