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三氟甲磺酸介导的分子间电环化反应合成吡唑啉及其在生物碱合成中的应用。

TfOH mediated intermolecular electrocyclization for the synthesis of pyrazolines and its application in alkaloid synthesis.

作者信息

Annes Sesuraj Babiola, Vairaprakash Pothiappan, Ramesh Subburethinam

机构信息

Department of Chemistry, School of Chemical and Biotechnology, SASTRA Deemed University Thanjavur Tamil Nadu India

出版信息

RSC Adv. 2018 Aug 24;8(53):30071-30075. doi: 10.1039/c8ra05702h.

DOI:10.1039/c8ra05702h
PMID:35546823
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9085413/
Abstract

TfOH mediated easy access to interesting pyrazolines starting from an aldehyde, phenylhydrazine and styrene has been developed. The scope of this synthetic methodology has been explored by synthesizing various 1,3,5-trisubstituted pyrazolines in very good yields with very high regioselectivity. The origin of regioselectivity has been explained by comparing the stability of possible intermediate carbocations. The synthetic utility of a green solvent has been explored by synthesizing some of pyrazolines in a DES medium. The synthetic application of the present methodology is employed in the synthesis of a pyrazoline alkaloid.

摘要

已经开发出由三氟甲磺酸介导，从醛、苯肼和苯乙烯出发轻松制备有趣的吡唑啉的方法。通过以非常高的区域选择性以非常好的产率合成各种1,3,5-三取代的吡唑啉，探索了这种合成方法的适用范围。通过比较可能的中间体碳正离子的稳定性来解释区域选择性的起源。通过在深共熔溶剂介质中合成一些吡唑啉，探索了绿色溶剂的合成效用。本方法的合成应用用于吡唑啉生物碱的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/0ed1ec24e758/c8ra05702h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/4e31bd66a538/c8ra05702h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/405932970253/c8ra05702h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/d9b8e89456dc/c8ra05702h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/0ed1ec24e758/c8ra05702h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/4e31bd66a538/c8ra05702h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/405932970253/c8ra05702h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/d9b8e89456dc/c8ra05702h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3962/9085413/0ed1ec24e758/c8ra05702h-s3.jpg

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本文引用的文献

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One-Pot Cascade Transformations of Zinc Trifluorodiazoethylide and α,β-Unsaturated Enones: Access to Trifluoromethylated Polycyclic Pyrazolines.一锅法三氟重氮乙酮与α,β-不饱和烯酮的级联转化：三氟甲基化多环吡唑啉的合成。
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