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hemetsberger indole synthesis wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 reaction mechanism 2 references toggle the table of contents hemetsberger indole synthesis 8 languages čeština deutsch español فارسی français bahasa indonesia தமிழ் 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction hemetsberger indole synthesis named after helfried hemetsberger reaction type ring forming reaction the hemetsberger indole synthesis also called the hemetsberger knittel synthesis is a chemical reaction that thermally decomposes a 3 aryl 2 azido propenoic ester into an indole 2 carboxylic ester 1 2 the hemetsberger indole synthesis yields are typically above 70 however this is not a popular reaction due to the lack of stability and difficulty in synthesizing the starting material reaction mechanism edit the mechanism is unknown however azirine 3 intermediates have been isolated the mechanism is postulated to proceed via a nitrene intermediate 4 references edit hemetsberger h knittel d 1972 synthese und thermolyse von α azidoacrylestern monatshefte für chemie 103 194 204 doi 10 1007 bf00912944 s2cid 91741917 gribble g w 2000 recent developments in indole ring synthesis methodology and applications j chem soc perkin trans 7 1045 1075 doi 10 1039 a909834h gilchrist t l 2001 activated 2h azirines as dienophiles and electrophiles pdf aldrichimica acta 34 2 51 archived from the original pdf on 15 may 2013 knittel d 1985 verbesserte synthese von α azidozimtsäure estern und 2h azirinen synthesis 1985 2 186 188 doi 10 1055 s 1985 31149 retrieved from https en wikipedia org w index php title hemetsberger_indole_synthesis oldid 1190392409 categories indole forming reactions name reactions hidden categories articles with short description short description matches wikidata use dmy dates from december 2023 this page was last edited on 17 december 2023 at 16 58 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents hemetsberger indole synthesis 8 languages add topic