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Nenitzescu synthesis of carbamate indole derivatives from N,N′-bis(methoxycarbonyl)-p-benzoquinone diimine

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Abstract

N,N′-Bis(methoxycarbonyl)-p-benzoquinone diimine reacted with 4-(cyclohex-1-en-1-yl)-and 4-(cyclopent-1-en-1-yl)morpholines in methylene chloride at room temperature to give morpholino-substituted cyclohexane-and cyclopentane-fused indole derivatives. Heating of the latter in boiling 10% hydrochloric acid led to the formation of methyl 6-(methoxycarbonylamino)-1,2,3,4,4a,9a-hexahydro-9H-carbazole-9-carboxylate and methyl 7-(methoxycarbonylamino)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole-4-carboxylate, respectively. The reaction of N,N′-bis(methoxycarbonyl)-p-benzoquinone diimine with 4-benzylaminopent-3-en-2-one in CH2Cl2 in the presence of BF3·Et2O on heating gave methyl 3-acetyl-2-methyl-(5-methoxy-carbonylamino)-1H-indole-1-carboxylate.

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Authors and Affiliations

  1. Astrakhan State University, ul. Tatishcheva 20 a, Astrakhan, 414000, Russia

    A. M. Borisov, N. A. Kamanina & A. V. Velikorodov

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  1. A. M. Borisov
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  2. N. A. Kamanina
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  3. A. V. Velikorodov
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Additional information

Original Russian Text © A.M. Borisov, N.A. Kamanina, A.V. Velikorodov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 415–417.

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Borisov, A.M., Kamanina, N.A. & Velikorodov, A.V. Nenitzescu synthesis of carbamate indole derivatives from N,N′-bis(methoxycarbonyl)-p-benzoquinone diimine. Russ J Org Chem 43, 414–416 (2007). https://doi.org/10.1134/S1070428007030141

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  • DOI: https://doi.org/10.1134/S1070428007030141

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