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Journal ArticleDOI

A novel thermal transformation of 2,4-di(N-aryl)amino-1,3,5-triazin-6-yl prop-2-ynyl ethers

01 Jan 1980-Tetrahedron Letters (Pergamon)-Vol. 21, Iss: 49, pp 4731-4734
TL;DR: In this paper, the isomeric 6-methylene imidazo [1,2-a] -1,3,5-triazines have been found to undergo a novel thermal transformation yielding the 6-yl propargyl ethers.
About: This article is published in Tetrahedron Letters.The article was published on 1980-01-01. It has received 9 citations till now. The article focuses on the topics: Propargyl & Aryl.
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Book ChapterDOI
01 Jan 1984

48 citations

Book ChapterDOI
TL;DR: The Claisen rearrangement has been widely used in the synthesis of natural heterocyclic products as discussed by the authors, and there are now several alkaloid syntheses in which the Claisen re-arrangement features as a key step.
Abstract: Publisher Summary The Claisen rearrangement of heteroaromatic allyl ethers shows many similarities to the rearrangement of simple benzenoid aromatic allyl ethers. Mechanistically, the reactions are for the most part genuine [3,3]-sigmatropic rearrangements, although the presence of nitrogen in the aromatic ring does allow alternative pathways to operate, and hence more than one product may be formed. However, these alternative products are usually easily rationalized on mechanistic grounds. One other difference between the Claisen rearrangement of heteroaromatic ally1 ethers (or thioethers) and their benzene counterparts is that the rearrangement product is often more stable in the one form than as the hydroxy (or mercapto) heteroaromatic compound. The Claisen rearrangement has been widely used in the synthesis of natural heterocyclic products. Although much of this work has been in the coumarin series, there are now several alkaloid syntheses in which the Claisen rearrangement features as a key step. Indications are that the Claisen rearrangement continues to hold an important role in organic chemistry.

38 citations

Journal ArticleDOI
TL;DR: A new method for the synthesis of dihydroimidazo[1,2-a][1,3,5]triazin-4(6H)-ones via copper(I)-catalyzed hydroamination was developed and for the first time, iodoalkynes were shown to participate in the copper( I)-catalystzed intramolecular hydroamination reaction with exclusive formation of E-isomers.
Abstract: A new method for the synthesis of dihydroimidazo[1,2-a][1,3,5]triazin-4(6H)-ones via copper(I)-catalyzed hydroamination was developed. In addition, for the first time, iodoalkynes were shown to participate in the copper(I)-catalyzed intramolecular hydroamination reaction with exclusive formation of E-isomers.

28 citations

Book ChapterDOI
01 Jan 1984

14 citations

Book ChapterDOI
01 Jan 1996

14 citations