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喹唑啉的碱介导螺环化反应：螺环异吲哚啉酮二氢喹唑啉酮的一步合成

Base mediated spirocyclization of quinazoline: one-step synthesis of spiro-isoindolinone dihydroquinazolinones.

作者信息

Venkateshwarlu Rapolu, Murthy V Narayana, Tadiparthi Krishnaji, Nikumbh Satish P, Jinkala Rajesh, Siddaiah Vidavalur, Madhu Babu M V, Rama Mohan Hindupur, Raghunadh Akula

机构信息

Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy's Laboratories Ltd. Hyderabad 500049 India.

Department of Organic Chemistry and FDW, Andhra University Visakhapatnam 530045 India

出版信息

RSC Adv. 2020 Mar 4;10(16):9486-9491. doi: 10.1039/c9ra09567e. eCollection 2020 Mar 2.

DOI:10.1039/c9ra09567e
PMID:35497232
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9050170/
Abstract

A novel approach for the spiro-isoindolinone dihydroquinazolinones has been demonstrated from 2-aminobenzamide and 2-cyanomethyl benzoate in the presence of KHMDS as a base to get moderate yields. The reaction has been screened in various bases followed by solvents and a gram scale reaction has also been executed under the given conditions. Based on the controlled experiments a plausible reaction mechanism has been proposed. Further the substrate scope of this reaction has also been studied.

摘要

在KHMDS作为碱的存在下，由2-氨基苯甲酰胺和2-氰基甲基苯甲酸酯已经证明了一种合成螺异吲哚啉酮二氢喹唑啉酮的新方法，可获得中等产率。该反应已在各种碱中进行筛选，随后在不同溶剂中进行，并且在给定条件下还进行了克级规模的反应。基于对照实验，提出了一种合理的反应机理。此外，还研究了该反应的底物范围。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/062d2bb60d69/c9ra09567e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/546dd67ce6ee/c9ra09567e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/9442277d79e9/c9ra09567e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/63b5c62d2d4a/c9ra09567e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/ef66342a131b/c9ra09567e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/0ebbacda2bcd/c9ra09567e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/062d2bb60d69/c9ra09567e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/546dd67ce6ee/c9ra09567e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/9442277d79e9/c9ra09567e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/63b5c62d2d4a/c9ra09567e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/ef66342a131b/c9ra09567e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/0ebbacda2bcd/c9ra09567e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/faf3/9050170/062d2bb60d69/c9ra09567e-s3.jpg

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Rh(III)-Catalyzed Diastereodivergent Spiroannulation of Cyclic Imines with Activated Alkenes.铑（III）催化的环状亚胺与活化烯烃的非对映选择性螺环化反应。
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