Narceine imide thermal decomposition

Thermal decomposition of narceine imide methiodide 73a in the presence of 30% aqueous potassium hydroxide afforded 91.4% of a mixture of ZjE-narceone imides 74, along with the azaazulenone 75 (R = OMe) (1.5%), which was also formed (8%) from 74 under the same conditions (75CCC681). 

Thermal decomposition of narceine imide methohydroxide (158) affords a mixture of (Z)- and (E)-narceone imides (159) together with a smaller amount of the dibenzyl dibenzopyrrocoline derivative (160). Cyclization of the narceone imides (159) in acid gave (160) (cf. Scheme 16) while cyclization in an alkaline medium gave the previously reported benzazepine derivative (161) (cf. Vol. 5). The structure of anhydro-N-oxynarceine (162 R =H R —OMe), which is obtained by refluxing... 

Thermal decomposition of narceine imide methiodide in the presence of 30% potassium hydroxide yields the Hofmann products 28 and 29, as well as the aporhoeadane derivative 30 which can be further reduced to 31 and 32 ... 

In contrast, thermal decomposition of narceine imide methohydroxide gives a 55% yield of 28 and 29, as well as a small amount of the rearranged lactam 33. ... 

---

See also in sourсe #XX -- [ , ]

---