Some Reactions with Indane‐1,3‐dione: A Facile Synthesis of Pentacycline Heterocyclic Analogues

Abstract

Indane‐1,3‐dione 1 reacts with salicylaldehyde 5 and malononitrile 3 to afford 6‐amino‐7‐imino‐7H‐indeno‐[2′,1′:5,6]‐pyrano‐[3,4‐c]‐chromene 6, which could be transformed into the corresponding 7‐oxo derivative 7. 2‐(3‐Oxoindan‐1‐ylidene)‐malononitrile 10 couples with the diazonium salts 8, 14, and 15 to afford after cyclization the indeno‐[2,1‐c]‐pyridazine 13 and the indeno‐[2′,1′:3,4]‐pyridazino‐[1,6‐a]‐quinazoline derivatives 20 and 21, respectively.

Indane-1,3-Dione: From Synthetic Strategies to Applications

“…Engineering around the Ketone Groups 2.2.1. Functionalization with Cyano Groups 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile 28 [24][25][26][27][28] and 2,2 -(1H-indene -1,3(2H)-diylidene)dimalononitrile 29 [28][29][30] can be synthesized by a Knoevenagel reaction of malononitrile 27 on 4 in ethanol using sodium acetate or piperidine as the bases. In the two cases, an excess of malononitrile was used, and the selection between the di-and the tetracyano-substituted derivative could be obtained by controlling the reaction temperature.…”

“…Notably, tetracyclines are efficient as antibiotics and anti-malarial drugs, and these structures have also been identified as being beneficial of various pathologies such as cancers or Parkinson's disease. Due to the increasing resistance of microbes to antimicrobials used from long ago, analogues to tetracyclines are actively researched, and a series of pentacyclines comprising the indane-1,3-dione motif have been synthesized [25]. The synthesis was relatively straightforward since the combination of malononitrile 27, salicylaldehyde 167 and indane-1,3-dione 4 in a one-pot procedure furnished 6-amino-7-imino-7H-indeno [2 ,1 :5,6]pyrano [3,4- The one-pot synthesis of pentacyclines was not limited to 4 as the starting material, and another derivative 172 was also prepared starting from 28 following two different synthetic routes in order to confirm its chemical structure (see Scheme 29).…”

Progress in Multicomponent Reactions Involving 1,3-Indanedione

“…文献报道, 茚并异喹啉衍生物具有对拓扑异构酶 I 的潜在抑制活性(Top1) [68] , 是新型 Top1 抑制剂, 具有良 好的药代动力学特征和化学稳定性 [69] . 2017 年, 姚清发 课题组 [70] [72][73] , 而 N-H…O＝C 氢键的存在使 C＝O 的反应活性降低无法成环, 必须先将 1,3-茚满二 酮与丙二腈缩合, 得到 2-(3-氧代茚满-1-亚基)-丙二腈 (154) [74] , 再与吡啶-4-重氮氯化物进行偶联, 在偶联条 [77] . 2011 年, Elliott 课题组 [3] 实现 在高氯酸锂、催化剂三乙胺存在下, 微波辅助下无溶剂 [78] , 受到广泛关注.…”