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F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
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] nitrene intermediate.[4]
References
[ edit ]
^ 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 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Hemetsberger_indole_synthesis&oldid=1190392409 " C a t e g o r i e s : ● R i n g f o r m i n g r e a c t i o n s ● I n d o l e f o r m i n g r e a c t i o n s ● N a m e r e a c t i o n s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● U s e d m y d a t e s f r o m D e c e m b e r 2 0 2 3
● T h i s p a g e w a s l a s t e d i t e d o n 1 7 D e c e m b e r 2 0 2 3 , a t 1 6 : 5 8 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
