UZH-Logo

Maintenance Infos

A ring enlargement from seven- to ten-membered-ring sulfonamide derivatives


Orahovats, Alexander S; Bratovanov, Svetoslav B; Linden, Anthony; Heimgartner, Heinz (1996). A ring enlargement from seven- to ten-membered-ring sulfonamide derivatives. Helvetica Chimica Acta, 79(4):1121-1128.

Abstract

The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1a) with 4,S-dihydro-7,8-dimethoxy-l,2-benzothiazepin-3-one 1,1-dioxide (4) in dioxane at room temperature gave the correspondingly substituted 4H-1,2,5- benzothiadiazecin-6-one 1,1-dioxide 5a in 64% yield (Scheme 2). The structure of this novel ten-membered ring-enlargement product was established by X-ray crystallography (Fig.). Under more vigorous conditions (refluxing dichloroethane), 5a was formed together with the isomeric 6a, both in low yield. The 3-(dimethylamino)-2H-azirines 1b and 1c reacted sluggishly to give the two isomeric ring-enlargement products of type 5 and 6 in yields of 24-29 % and 2-4 % , respectively (Table 1 ). Even less reactive is 2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine (1d), which reacted with 4 in MeCN only at 65°. Under these conditions, besides numerous decomposition products, only traces of 5d and 6d were formed. No ring enlargement was observed with the sterically crowded 1e, which bears an isopropyl group at C(2).

Abstract

The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1a) with 4,S-dihydro-7,8-dimethoxy-l,2-benzothiazepin-3-one 1,1-dioxide (4) in dioxane at room temperature gave the correspondingly substituted 4H-1,2,5- benzothiadiazecin-6-one 1,1-dioxide 5a in 64% yield (Scheme 2). The structure of this novel ten-membered ring-enlargement product was established by X-ray crystallography (Fig.). Under more vigorous conditions (refluxing dichloroethane), 5a was formed together with the isomeric 6a, both in low yield. The 3-(dimethylamino)-2H-azirines 1b and 1c reacted sluggishly to give the two isomeric ring-enlargement products of type 5 and 6 in yields of 24-29 % and 2-4 % , respectively (Table 1 ). Even less reactive is 2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine (1d), which reacted with 4 in MeCN only at 65°. Under these conditions, besides numerous decomposition products, only traces of 5d and 6d were formed. No ring enlargement was observed with the sterically crowded 1e, which bears an isopropyl group at C(2).

Citations

9 citations in Web of Science®
11 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 25 Nov 2013
0 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1996
Deposited On:25 Nov 2013 08:19
Last Modified:05 Apr 2016 17:11
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Professor Hans E. Schmid-Stiftung
Publisher DOI:https://doi.org/10.1002/hlca.19960790420

Download

[img]
Content: Published Version
Filetype: PDF - Registered users only
Size: 446kB
View at publisher

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations