The Reaction of Oxalyl Chloride with Amides. I. The Preparation of Furanone Amines

Speziale, A. J.; Smith, Lowell R.

doi:10.1021/jo01059a054

Cited by 131 publications

(24 citation statements)

References 1 publication

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“…The starting materials, 1-(2-bromobenzoyl)-3-phenylthiourea 3-phenylureas 1, 1-(2-chlorobenzoyl)-3-phenylthiourea 3-phenylureas 2 and 1-(2-bromobenzoyl)-3-phenylurea 7, were prepared from the respective o-halogenobenzoic acids using literature procedures. 9,10 The starting materials were reacted under conditions shown to favour S RN 1, 2 i.e. potassium tertbutoxide (t-BuOK), DMF, heat and light catalysis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1H-quinazoline-4-ones using intramolecular aromatic nucleophilic substitution

Bowman¹,

Heaney²,

Smith³

2003

Arkivoc

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The anions of 1-(2-bromobenzoyl)-3-phenylthiourea 1, 1-(2-chlorobenzoyl)-3-phenylthiourea 2 and 1-(2-bromobenzoyl)-3-phenylurea 8 undergo intramolecular nucleophilic substitution (putative S N Ar mechanism), and not intramolecular S RN 1 substitution, to yield 1-phenyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one 6 and 1-phenyl-1H-quinazoline-2,4-dione 9 respectively. Under the same reaction conditions with the addition of copper(I) iodide, phenylthioureas 1 and 2 gave a rearrangement to the respective 2-halogeno-N-phenylbenzamides.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 1H-quinazoline-4-ones using intramolecular aromatic nucleophilic substitution

Bowman¹,

Heaney²,

Smith³

2003

Arkivoc

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“…To a stirred suspension of the NSAID amide (30 mmol) in 1,2-dichloroethane (100 mL) was added oxalyl chloride (36 mmol) and refluxed for 16 h to get the corresponding acyl isocyanate 43. 24) The reaction mixture was cooled to room temperature. A solution of 36 (30 mmol) in 1,2-dichloroethane (10 mL) was added to the above mixture and the mixture was stirred for 16 h at room temperature to generate the corresponding imide containing prodrugs 26-30.…”

Section: -(2-((2-(nitrooxy)ethyl)disulfanyl)ethoxy)-2-oxoethyl-2-(1-mentioning

confidence: 99%

NO-NSAIDs. Part 3: Nitric Oxide-Releasing Prodrugs of Non-steroidal Anti-inflammatory Drugs

et al. 2012

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“…However, the dominant commercial process utilizes the reaction of carboxamides with oxalyl chloride [79-37-8]. Cyclic intermediates have been observed in these reactions which generally give a high yield of the desired products (86).…”

Section: Specialty Isocyanatesmentioning

confidence: 99%

Isocyanates, Organic

Richter¹,

Priester²

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Isocyanates are highly reactive compounds which have found wide utilities in synthetic transformations and industrial applications. These materials are synthesized by reaction of primary aliphatic or aromatic amines and phosgene (carbonyl dichloride) to form carbamoyl chlorides which are subsequently pyrolyzed to the desired isocyanates. A characteristic reaction of isocyanates and alcohols to form carbamates (urethanes) has been used for the qualitative identification of the latter. Extension of this reaction to difunctional isocyanates and difunctional or polyfunctional alcohols is the basis of the polyurethane industry, with products ranging from flexible and rigid insulating foams to thermoplastic elastomers, coatings, and adhesives, as well as a variety of automotive and recreational products. p ‐Toluenesulfonyl isocyanate is used in the synthesis of drugs for diabetics. A unique feature of isocyanates is their tendency to oligomerize or polymerize in presence of catalysts. In addition, isocyanates easily form adducts with carbodiimides, isothiocyanates, ketenes, or with substrates containing activated or bonds. Low boiling isocyanates are strong lachrymators and irritants. Several isocyanates and their precursors have been identified as mutagens. Guidelines for safe handling of isocyanates are discussed. Vol. 14, pp. 902–934, 100 refs. to January 15, 1993.

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The Reaction of Oxalyl Chloride with Amides. I. The Preparation of Furanone Amines

Cited by 131 publications

References 1 publication

Synthesis of 1H-quinazoline-4-ones using intramolecular aromatic nucleophilic substitution

Synthesis of 1H-quinazoline-4-ones using intramolecular aromatic nucleophilic substitution

NO-NSAIDs. Part 3: Nitric Oxide-Releasing Prodrugs of Non-steroidal Anti-inflammatory Drugs

Isocyanates, Organic

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