62348-24-7

Usage

Chemical Properties

Colourless liquid

InChI:InChI=1/C5H4ClNO2/c1-3-4(5(6)8)9-2-7-3/h2H,1H3

Upstream product

• 2510-32-9 4-methyl-1,3-oxazole-5-carboxylic acid 
• 20485-39-6 ethyl 4-methyloxazole-5-carboxylate 

Downstream Products

• 90620-27-2 N-allyl-4-methyloxazole-N-phenyl-5-carboxamide 
• 90620-28-3 4-Methyl-oxazole-5-carboxylic acid ((E)-but-2-enyl)-phenyl-amide 
• 87205-06-9 N-(3-butenyl)-4-methyl-N-phenyloxazole-5-carboxamide 
• 90620-25-0 N-allyl-4-methyloxazole-5-carboxamide 
• 170959-55-4 1-(4-methyloxazole-5-carboxyl)-4-phenylthiosemicarbazide 
• 911297-36-4 (4-methyl-oxazol-5-yl)-[2-(1-methyl-3-trimethylsilanyl-prop-2-ynyl)-phenyl]methanone 
• 911297-48-8 (4-methyl-oxazol-5-yl)-[2-(1-methyl-prop-2-ynyl)-phenyl]methanone 
• 911297-49-9 6-[2-(4-methyl-oxazole-5-carbonyl)-phenyl]-hept-2-en-4-ynoic acid ethyl ester 
• 170959-40-7 5-(4-methyl-5-oxazoyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 170959-47-4 5-(4-methyl-5-oxazoyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 170959-39-4 3-(4-methyl-5-oxazoyl)-4-phenyl-5-methylthio-4H-1,2,4-triazole 
• 101708-13-8 5-hydroxy-4-hydroxymethyl-6-methylpyrimidine 
• 87205-04-7 8-methyl-1-oxo-2-phenylpiperidino<3,4-c>pyridine 
• 87205-05-8 10-methyl-2-oxo-3-phenyl-11-oxa-3,9-diazatricyclo<6.2.1.0>undec-9-ene 

Relevant academic research and scientific papers

Method for synthesizing furanosteroids

The present invention is a method for synthesizing furanosteroids. The method involves intramolecular Diels-Alder/retro-Diels-Alder reaction and tautomerization of a functionalized alkyne oxazole to produce a furo[2,3-b]phenol derivative which is elaborated by intermolecular and intramolecular condensations to generate ring-A of the furanosteroid. Furanosteroids and pharmaceutical compositions containing the same are also provided.

Studies on the synthesis of furanosteroids. I. Viridin models

Alkyne oxazoles of general structure I are transformed directly to furo[2,3-b]phenol derivatives II by a sequence involving intramolecular Diels-Alder/retro-Diels-Alder reaction followed by tautomerization. Suitably functionalized phenols II undergo an intramolecular phenol-dienone-aldol condensation, generating the A,B,E-ring skeleton III characteristic of the viridin (1) class of furanosteroids.

Oxazole to Pyrimidine Ring Transformation: Synthesis of Potential Pyridoxine Antagonists

The reaction of 4-methyloxazole-5-carbonyl chloride (I) with diazomethane gives 5-diazoacetyl-4-methyloxazole (II).Decomposition of II in methanol containing BF3-etherate provides the α-keto ether, 5-(methoxyacetyl)-4-methyloxazole (III).The α-ketol 5-(hydroxyacetyl)-4-methyloxazole (IV), obtained by decomposition of II in aq. acid, on treatment with dihydropyran in the presence of pyridinium toluene-p-sulfonate furnishes 4-methyl-5-oxazole (V).Warming III and V in methanolic ammonia in a sealed tube provides 5-hydroxy-4-methoxymethyl-6-methylpyrimidine (VI) and 5-hydroxy-6-methyl-4pyrimidine (VII), respectively.Acid-catalysed removal of the tetrahydropyranyl moiety from VII affords 5-hydroxy-4-hydroxymethyl-6-methylpyrimidine (VIII).

Intramolecular Diels-Alder Reaction of Alkenyl Oxazole-5-carbamates and N-Alkenyl-oxazole-5-carboxamides

Intramolecular cycloaddition of N-allyl-4-methyloxazole-5-carboxamides (1) gave the corresponding 6a-acetyl-2-hydroxy-6-oxotetrahydrofuropyrrolidines (3).Tricycloadducts (6) were obtained by the intramolecular Diels-Alder reaction of N-(3-butenyl)-