Synthesis of novel precursors of Pfitzinger reaction: A facile one-pot strategy to the synthesis of quinoline carboxylic acid derivatives of pyrazolo-carbazoles and azacarbazoles

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• 作者：RUCHI TYAGI (1)
  BHAWANI SINGH (1) bsyadav2000@gmail.com
  D KISHORE (1)
• 关键词：Japp– ; Klingemann reaction – ; tetrahydropyrazolo[4 ; 3 ; b]carbazol ; 6(1H) ; one – ; 9 ; benzyl ; 5 ; 7 ; 8 ; 9 ; tetrahydropyrido[2′ ; 3′ ; ; 4 ; 5]pyrrolo[2 ; 3 ; f]indazol ; 6(1H) ; one – ; Pfitzinger reaction – ; quinoline 4 ; carboxylic acid
• 刊名：Journal of Chemical Sciences
• 出版年：2012
• 出版时间：March 2012
• 年：2012
• 卷：124
• 期：2
• 页码：431-435
• 全文大小：173.5 KB
• 参考文献：1. Caruso A, Voisin-Chiret S A, Lancelot J-C, Sinicropi M S, Garofalo A and Rault S 2008 Molecules 13(6) 1312
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• 作者单位：1. Department of Chemistry, Banasthali University, Banasthali, (Rajasthan)-304022 India
• ISSN：0973-7103

文摘

Interaction of 5-indazolyldiazonium chloride 2 with 2-hydroxymethylidene cyclohexanone 5 and N-benzyl-3-hydroxymethylidene-4-piperidone 6 under the conditions of Japp–Klingemann reaction, followed by Fischer-indolization of the resulting hydrazones, formed the 5,7,8,9-tetrahydropyrazolo[4,3-b]carbazol-6(1H)-one 9 and 9-benzyl-5,7,8,9-tetrahydropyrido[2′,3′:4,5]pyrrolo[2,3-f]indazol-6(1H)-one 10, respectively. Pfitzinger reaction of 9 and 10 with isatin in alkali afforded the corresponding quinoline carboxylic acid derivatives 12 and 13, respectively.