Regioselective, one-pot, multi-component, green synthesis of substituted benzo[c]pyrazolo[2,7]naphthyridines

Ashraf Abida; Shafiq Zahid; Mahmood Khalid; Yaqub Muhammad; Rauf Waqar

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Regioselective, one-pot, multi-component, green synthesis of substituted benzo[c]pyrazolo[2,7]naphthyridines

机译：替代苯并[C]吡唑的区域选择性，单锅，多组分，绿色合成[2,7]萘吡啶

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An efficient and environmentally benign synthetic protocol has been developed for the synthesis of benzo[c]pyrazolo[2,7]naphthyridine derivatives through regioselective multi-component "on-water" reaction of isatin, malononitrile and 3-aminopyrazole. The Knoevenagel condensation of isatin with malononitrile resulted in the formation of arylidene, which subsequently underwent Michael addition with 3-aminopyrazole followed by basic hydrolysis, cyclization, decarboxylation and aromatization to give the target naphthyridines in good to excellent yields. The one-pot multi-component protocol was also employed to obtain the said naphthyridines in a lower yield (10-15%) than obtained by basic hydrolysis of spiro-intermediates. The present study shows attractive features such as the use of water as a green solvent, short reaction time, reduced waste products and transition metal free C-C and C-N bond formation. The structures of the synthesized derivatives were established through FTIR, H-1-NMR, C-13-NMR spectroscopy and ESI-mass spectrometry.

机译：通过ISATIN，丙二腈和3-氨基吡唑的区域选择性多组分“在水”反应，开发了一种高效和环境良性的合成方案，用于合成苯并[C]吡唑啉[2,7]萘吡啶衍生物。 Isatin用丙二腈的knoevenagel缩合导致亚胺的形成，随后与3-氨基吡唑加成进行迈克尔加成，然后进行碱性水解，环化，脱羧和芳香化，得到靶标萘吡啶，良好至优异的产率。还采用单盆多组分方案，以获得低产率（10-15％）的上述萘啶，而不是通过螺旋中间体的基本水解而获得的。本研究表明，诸如使用水作为绿色溶剂，短反应时间，减少废物和过渡金属的游离金属和C-N键形成等特征。通过FTIR，H-1-NMR，C-13-NMR光谱和ESI质谱法建立合成衍生物的结构。

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《RSC Advances》 |2020年第10期|共13页
作者
Ashraf Abida; Shafiq Zahid; Mahmood Khalid; Yaqub Muhammad; Rauf Waqar;
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Bahauddin Zakariya Univ Inst Chem Sci Multan Pakistan;

Bahauddin Zakariya Univ Inst Chem Sci Multan Pakistan;

Bahauddin Zakariya Univ Inst Chem Sci Multan Pakistan;

Bahauddin Zakariya Univ Inst Chem Sci Multan Pakistan;

NIBGE POB 577 Faisalabad Pakistan;

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正文语种 eng
中图分类化学;
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1. Regioselective, one-pot, multi-component, green synthesis of substituted benzo[c]pyrazolo[2,7]naphthyridines [J] . Ashraf Abida, Shafiq Zahid, Mahmood Khalid, RSC Advances . 2020,第10期

机译：替代苯并[C]吡唑的区域选择性，单锅，多组分，绿色合成[2,7]萘吡啶
2. Naphthyridines part 4: unprecedented synthesis of polyfunctionally substituted benzo[c][2,7]naphthyridines and benzo[c]pyrimido[4,5,6-ij][2,7]naphthyridines with structural analogy to pyrido[4,3,2-mn]acridines present in the marine tetracyclic pyridoacridine alkaloids [J] . Mekheimer Ramadan A., Al-Sheikh Mariam A., Medrasi Hanadi Y., Molecular diversity . 2018,第1期

机译：萘萘啶部分4：前所未有的多官能取代的苯并[c] [2,7]萘啶和苯并[4,5,6-IJ] [4,5,6-IJ] [4,7]萘吡啶与吡啶的结构类比[4,3，海洋四环吡啶吖啶生物碱中存在的2-Mn]吖啶
3. A facile one-pot regioselective synthesis of functionalized novel benzo[f] chromeno[4,3-b][1,7]naphthyridines and benzo[f][1,7]naphthyridines via an imino Diels-Alder reaction [J] . Arepalli Sateesh Kumar, Park Byeongwoo, Jung Jae-Kyung, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2017,第5期

机译：官能化新型苯并[F] Chromeno [4,3-B] [1,7]萘啶和苯并[1,7]萘吡啶，通过氨基Diels-桤木反应进行官能化新型苯并[4,3-B] [1,7]萘啶
4. Synthesis and Metal Complexation Behavior of Benzo-Annulated Naphthyridine Derivatives with Phosphine Moieties [C] . Hidetoshi Ohta, Kohta Takahama, Minoru Hayashi 日本化学会春季年会講演予稿集 . 2018

机译：磷酸盐部分苯并计算萘萘啶衍生物的合成与金属络合行为
5. New developments toward the synthesis of heterocycles and applications in green chemistry. I. A simple and essentially one-pot synthesis of N-aminated heterocycles using phase transfer catalyst (Aliquat-336). II. Synthesis of pharmaceutically important pyrrole derivatives. III. Applications in green chemistry: Surfactant-mediated environmentally friendly cleavage of aromatic esters and trans-esterification under solvent-free neutral conditions . [D] . Patel, Nitinchandra. 2005

机译：杂环合成的新进展及其在绿色化学中的应用。 I.使用相转移催化剂（Aliquat-336）简单且基本上一锅合成N-胺化的杂环。二。药学上重要的吡咯衍生物的合成。三，在绿色化学中的应用：在无溶剂的中性条件下，表面活性剂介导的环境友好的芳族酯裂解和酯交换反应。
6. Multi-Component One-Pot Synthesis and Antimicrobial Activities of 3-Methyl-14-diphenyl-7-thioxo-4689-tetrahydro-pyrazolo54-bpyrimidino54-epyridine-5-one and Related Derivatives [O] . Talaat I. El-Emary, Shawkat A. Abd El-Mohsen 2012

机译：3-甲基-14-二苯基-7-thioxo-4689-四氢-吡唑并54-b嘧啶并54-e的多组分一锅合成及抗菌活性吡啶-5-酮及相关衍生物
7. A three step one-pot regioselective synthesis of highly substituted pyrazolo1,5-apyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation [O] . Shunan Kaping, Philippe Helissey, Jai Narain Vishwakarma 2020

机译：在超声辐射下，在水性介质中辅助KHSO4辅助KHSO4的高度取代吡唑1,5-A嘧啶的三步一孔区域合成

Regioselective, one-pot, multi-component, green synthesis of substituted benzo[c]pyrazolo[2,7]naphthyridines

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