An operationally facile and efficient protocol has been developed for the construction of various 1,3‐oxazole‐containing heterocycles with excellent yields of up to 94 %. -catalyzed synthesis of imidazo[1,2-a]pyridines via sp . TCI verwendet Cookies, um Ihre Benutzerfreundlichkeit zu personalisieren und zu verbessern. Experimental procedure 2): Diphenylphosphoryl azide (0.87 mL, 4.04 mmol) is added to a solution of alcohol 1 (98 mg, 0.40 mmol), PPh 3 (211 mg, 0.81 mmol) and DEAD (0.37 mL, 40% in toluene, 0.81 mmol) in THF (5 mL) and the reaction is stirred at room temperature for 24 h. As a service to our authors and readers, this journal provides supporting information supplied by the authors. . and you may need to create a new Wiley Online Library account. Use the link below to share a full-text version of this article with your friends and colleagues. 2.3. Other hazards No additional information available 2.4. A new convenient reagent for a modified Curtius reaction, 2)A Versatile Enantioselective Synthesis of Barrenazines. and you may need to create a new Wiley Online Library account. The synthetic utility of this transformation is also extended through a scaled‐up synthesis and C−H activation. Contact Us View the article PDF and any associated supplements and figures for a period of 48 hours. Unlimited viewing of the article/chapter PDF and any associated supplements and figures. Structure: CAS Number: 26386-88-9 Molecular Weight: 275.20 g/mol Appearance: Colorless to light yellow liquid Boiling Point: 157 C Density: 1.277 g/mL DPPA is very toxic and a potential explosive like most other azide compounds. , DPPA undergoes pseudohalogen replacement of the azido group by treatment with nucleophilic reagents, such as ammonia and various amines. TCI wishes to warn its customers about the possibility of such fraudulent activities. You can easily unsubscribe at any time. Li enolates unsubstituted at the ɑ-position can undergo diazo-transfer reactions to give the diazo carbonyl derivatives. Keywords: Azide formation, Cyclizations, Peptide synthesis Organic Azides and Azide Sources Since the preparation of the first organic azide, phenyl azide, by Peter Griess in 1864 this energy-rich and versatile class of compounds has enjoyed considerable interest. DPPA decomposes at >200 C. 1) Patent Reference: WO2007117607, page 312, (12.9 MB), 2) Patent Reference: WO2015144799, page 343, (18.8 MB), 3) Pearson, A. J.; Roush, W. R.; Handbook of Reagents for Organic Synthesis, Activating Agents and Protecting Groups, 4) Wikipedia: Diphenylphosphoryl azide (link), 5) www.sigmaaldrich.com: Diphenyl phosphoryl azide (link). Diphenylphosphoryl azide (DPPA) is an organic compound. Finally, the acyl azide reacts in the normal manner to give the urethane. Heute anmelden! Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts, Total Synthesis of Camptothecin and Related Natural Products by a Flexible Strategy, 1)Phosphorus in organic synthesis-VII: Diphenyl phosphorazidate (DPPA). Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, I have read and accept the Wiley Online Library Terms and Conditions of Use, ajoc201700147-sup-0001-misc_information.pdf. Diphenylphosphoryl azide (DPPA) is toxic and an irritant. It is widely used as a reagent in the synthesis of other organic compounds. The resulting mixture . If your information is correct and you are still not able to view the requested SDS, Any queries (other than missing content) should be directed to the corresponding author for the article. This protocol proceeds through a diphenylphosphoryl azide (DPPA)‐mediated reaction cascade on substituted 2‐aminonicotinic acids/2‐aminoanthranilic acids with ethyl isocyanoacetate/p‐toluenesulfonylmethyl isocyanides by forming C−C, C−O, and C−N bonds in a single operation. Wenn Ihre Eingabe korrekt ist und Sie dennoch das Analysezertifikat nicht anzeigen können P260 : Do not breathe dust/ fume/ gas/ mist/ vapours/ spray. If you have previously obtained access with your personal account, please log in.