6-(2-Nitrostyryl)pyran-2-ones 3 are converted into 6-(indol-2-yl)pyran-2-ones 4 by reduction of the nitro group with triethyl phosphite and consequent addition of the nitrene intermediate to the styryl double bond. Compounds 4 undergo a rather unusual, base-catalysed, rearrangement leading to azepino[1,2-a] indol-6-ones 5.
α-Pyrones. Part 4. synthesis of 3-benzoylamino-6-(indol- 2-yl)pyran-2-ones and their rearrangement to substituted azepino[1,2-a]indole-6- ones: Unusual neighbouring group participation / M.L. Gelmi, D. Pocar, F. Vago. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :8(1993), pp. 969-973.
α-Pyrones. Part 4. synthesis of 3-benzoylamino-6-(indol- 2-yl)pyran-2-ones and their rearrangement to substituted azepino[1,2-a]indole-6- ones: Unusual neighbouring group participation
M.L. GelmiPrimo
;D. PocarSecondo
;
1993
Abstract
6-(2-Nitrostyryl)pyran-2-ones 3 are converted into 6-(indol-2-yl)pyran-2-ones 4 by reduction of the nitro group with triethyl phosphite and consequent addition of the nitrene intermediate to the styryl double bond. Compounds 4 undergo a rather unusual, base-catalysed, rearrangement leading to azepino[1,2-a] indol-6-ones 5.
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