Synthesis of 4H‐Benzo[e][1,3]oxazin‐4‐ones by a Carbonylation–Cyclization Domino Reaction of ortho‐Halophenols and Cyanamide

Åkerbladh, Linda; Chow, Shiao Y.; Odell, Luke R.; Larhed, Mats

doi:10.1002/open.201700130

Cited by 11 publications

(7 citation statements)

References 48 publications

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“…Recently, this approach has been extended to the synthesis of 4H-benzo[e] [1,3]oxazin-4-ones from 2-iodophenols or 2bromophenols by using either Mo(CO) 6 or a range of nongaseous CO-sources. 128 In 2017, we developed a four-component carbonylation/amination two-step one-pot protocol for the synthesis of N-acylguanidines (Scheme 26). 129 The reaction was initiated by the formation of an N-cyanobenzamide intermediate from the carbonylative coupling of aryl iodides and bromides with cyanamide.…”

Section: Scheme 23 Palladium-catalyzed Carbonylative Annulation Reaction For the Synthesis Of 2(1h)-quinolonesmentioning

confidence: 99%

Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions

Åkerbladh

Odell

Larhed

2018

Synlett

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This account summarizes Pd(0)-catalyzed Mo(CO)6-mediated gas-free carbonylative reactions published in the period October 2011 to May 2018. Presented reactions include inter- and intramolecular carbonylations, carbonylative cross-couplings, and carbonylative multicomponent reactions using Mo(CO)6 as a solid source of CO. The presented methodologies were developed mainly for small-scale applications, avoiding the problematic use of gaseous CO in a standard laboratory. In most cases, the reported Mo(CO)6-mediated carbonylations were conducted in sealed vials or by using two-chamber solutions.1 Introduction2 Recent Developments2.1 New CO Sources2.2 Two-Chamber System for ex Situ CO Generation2.3 Multicomponent Carbonylations3 Carbonylations with N and O Nucleophiles4 Carbonylative Cross-Coupling Reactions with Organometallics5 Carbonylative Cascade Reactions6 Carbonylative Cascade, Multistep Reactions7 Summary and Outlook

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Section: Scheme 23 Palladium-catalyzed Carbonylative Annulation Reaction For the Synthesis Of 2(1h)-quinolonesmentioning

confidence: 99%

Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions

Åkerbladh

Odell

Larhed

2018

Synlett

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“…Step 1: Synthesis of 2-methyl-4H-benzo[d] [1,3] oxazin-4-one [16] In this reaction, anthranilic acid [6] (0.01 M) was refluxed under anhydrous condition for 4 h using acetic anhydride as a solvent. The remaining unreacted acetic anhydride was distilled off to get product N-acetyl anthranilic acid.…”

Section: Synthesis Of (E)-3-(5-(((4-substitutedphenyl) Amino) Methyl)-134-thiadiazol-2-yl)-2styrylquinazolin-4(3h)-onementioning

confidence: 99%

Untitled

2021

IJPSCR

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The objective of the paper was to design and synthesize new derivatives of ((E)-3-(5-((substitutedphenylamino) methyl)-1,3,4-thiadiazol-2-yl)-2styrylquinazolin-4(3H)-one and evaluated for their anticonvulsant potential. Materials and Methods: Various syntheses of (E)-3-(5-(substitutedaminomethyl)-1,3,4-thiadiazol-2-yl)-2-styrylquinazolin-4(3H)-one derivatives have been synthesized by reacting 2-substituted benzoxazin-4-one with (E)-2-(4-Substituedstyryl)-4H-benzo [d] [1,3]oxazin-4-one. All synthesized compounds have been characterized by the infrared, 1H-NMR, and mass spectral analysis. Proposed compounds have been evaluated for anticonvulsant potential by subcutaneous pentylenetetrazole and maximal electroshock seizure model and compared with the reference drug phenytoin and carbamazepine. Neurotoxicity study of the synthesized compounds was also performed. Results and Discussion: The anticonvulsant evaluation of synthesized compound QNM-1, QNM-2, QNM-4, QNM-6, QNM-9, QNM-11, QNM-13, and QNM-15 has shown seizure protection at 100 mg/kg dose after 30 min and 4 h, so they have good onset of action as quickly reach brain and have prolonged action reveal that compound metabolized slowly, whereas compounds QNM-7, QNM-8, and QNM-12 were moderate active and reveal that their high concentration is required to cross blood-brain barrier. Compounds QNM-3, QNM-5, QNM-10, and QNM-14 were less active. Compounds having chlorine, bromine, fluorine, and nitro in the phenyl moiety have shown good activity when attached to para group but the addition of meta and ortho group of the same may provide least active compounds and in last fluorine compounds have shown comparative less active compounds. Conclusion: The pharmacological evaluation suggests that eight synthesized compounds have shown promising anticonvulsant potential and bulkier compounds can easily penetrate BBB to exert their effect.

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“…In addition, two-step method by refluxing the salicylamide with aroyl chloride in pyridine followed by cyclization of the isolated intermediate by hydrogen chloride. 99 Further, by carbonylation-cyclization of ortho-halophenols and cyanamide 100 or by treatment of the corresponding 2-hydroxycarboxamides with a formaldehyde/formic acid mixture, 101 the corresponding 4H-1,3-benzoxazin-4-ones were synthesized. The 2-trichloromethyl and 2-dichlorometylene-2H-1,3-benzoxazine derivatives were obtained via intramolecular cyclization of N-(α-aryloxytrichloroethyl)imidoyl chlorides through dehydrochlorination.…”

Section: Synthesis Of 2h-13-benzoxazin-4-onementioning

confidence: 99%

3,4-Dihydro-2H-1,3-benzoxazines and their oxo-derivatives - Chemistry and bioactivities

Eldin

2021

JSCS

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It must be stressed that the manuscript still has to be subjected to copyediting, typesetting, English grammar and syntax corrections, professional editing and authors' review of the galley proof before it is published in its final form. Please note that during these publishing processes, many errors may emerge which could affect the final content of the manuscript and all legal disclaimers applied according to the policies of the Journal.

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Synthesis of 4H‐Benzo[e][1,3]oxazin‐4‐ones by a Carbonylation–Cyclization Domino Reaction of ortho‐Halophenols and Cyanamide

Cited by 11 publications

References 48 publications

Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions

Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions

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3,4-Dihydro-2H-1,3-benzoxazines and their oxo-derivatives - Chemistry and bioactivities

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