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Topic: dibenzo[b,f][1,4]thiazepin-11(10H)-one formation  (Read 2448 times)

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Offline Mr. Piyush Limbad

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dibenzo[b,f][1,4]thiazepin-11(10H)-one formation
« on: January 14, 2013, 12:42:26 PM »
can dibenzo[b,f][1,4]thiazepin-11(10H)-one from N-phenyl benzamide?

Offline sjb

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Re: dibenzo[b,f][1,4]thiazepin-11(10H)-one formation
« Reply #1 on: January 14, 2013, 01:19:30 PM »
can dibenzo[b,f][1,4]thiazepin-11(10H)-one from N-phenyl benzamide?

Can it what? Sorry, the question doesn't make sense.

Offline Mr. Piyush Limbad

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Re: dibenzo[b,f][1,4]thiazepin-11(10H)-one formation
« Reply #2 on: January 18, 2013, 12:31:16 PM »

dibenzo[b,f][1,4]thiazepin-11(10H)-one can be prepared from N-phenyl benzamide and sulfur cyclization using Iodine as catalyst?

*MOD Edit* removed quote fields from responce
« Last Edit: January 18, 2013, 04:50:26 PM by Arkcon »

Offline Arkcon

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Re: dibenzo[b,f][1,4]thiazepin-11(10H)-one formation
« Reply #3 on: January 18, 2013, 04:47:53 PM »
Here is a reference for the synthesis of this particular anti-psychotic pharmaceutical:  http://en.wikipedia.org/wiki/Quetiapine#Synthesis

Maybe by looking at that synthesis, you can compare it to your plan, and see if your plan will still work, or not?
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline tomek

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Re: dibenzo[b,f][1,4]thiazepin-11(10H)-one formation
« Reply #4 on: January 21, 2013, 06:15:34 AM »
Some phenothiazines can be made that way. I don't know if it's going to work in this case, but you can close the ring as shown below (US 4879288) or Schmutz, J., Künzle, F., Hunziker, F. and Bürki, A. (1965), Neue Synthese von Lactamen der Dibenz[b,f]-1,4-thiazepin-, -oxazepin und Dibenz[b, e]-azepin-Reihe. 4. Mitteilung über siebengliedrige Heterocyclen. HCA, 48: 336–347. doi: 10.1002/hlca.19650480212


Offline orgopete

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Re: dibenzo[b,f][1,4]thiazepin-11(10H)-one formation
« Reply #5 on: January 22, 2013, 10:01:03 AM »

dibenzo[b,f][1,4]thiazepin-11(10H)-one can be prepared from N-phenyl benzamide and sulfur cyclization using Iodine as catalyst?


This seems rational. Sulfur can react as an electrophile and the anilide would be nucleophilic at the o/p positions. The more difficult reaction is an electrophilic reaction onto the benzamide ring from an electrophilic sulfur (R-S-I or RS+).
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