Ethyl 11a,12-Dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate

Lidia S Konstantinova,Mikhail A Tolmachev,В В Попов ,Олег А Ракитин

doi:10.3390/m1149

Lidia S Konstantinova, Mikhail A Tolmachev + Show 2 more

Open Access

https://doi.org/10.3390/m1149

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Abstract

The 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine heterocyclic system has been used in the construction of heteropropellanes, which attracted much attention not only on the possible modification of drugs, but also for novel materials with unusual and important physical properties. In this communication, the reaction of ethyl 2-(hydroxyimino)propanoate 1 with disulfur dichloride and o-aminophenol, which gave ethyl 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate in moderate yield, was described. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy, mass-spectrometry and X-ray analysis.

Highlights

Disulfur dichloride is a well-known and frequently used sulfurating agent [1,2]
We report the synthesis of previously unknown ethyl 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate, which unexpectedly formed in the reaction of ethyl 2-(hydroxyimino)propanoate with disulfur dichloride and o-aminophenol
The intensity data were integrated by the SAINT program and were corrected for absorption and decay (Bruker Daltonik Gmbh, Bremen, Germany) using electrospray ionization (ESI)

Summary

Introduction

Disulfur dichloride is a well-known and frequently used sulfurating agent [1,2]. Sometimes it may act as oxidizing agent as well, giving compounds without additional sulfur atoms [3]. It was discovered that by the reaction of substituted acetoximes, including ethyl. 2-(hydroxyimino)propanoate, with S2 Cl2 4-substituted 1,2,3-dithiazolium salts are formed, which by treatment with oxygen, sulfur and nitrogen nucleophiles afforded 1,2,3-dithiazole 5-ones, 5-thiones and 5-phenylimines, respectively [4]. We report the synthesis of previously unknown ethyl 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate, which unexpectedly formed in the reaction of ethyl 2-(hydroxyimino)propanoate with disulfur dichloride and o-aminophenol

Results and Discussion

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