One-step conversion of oxetane-fused to 1,3-oxazine-fused steroids

Andrea Hajnal, J. Wölfling, G. Schneider

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

In a ring-expansion reaction, alkyl and aryl nitriles, in the presence of tetrafluoroboric acid-diethyl ether complex, react with 3-methoxy-16β,17β-dihydro-4′H-oxeto[3′,2′:16,17] estra-1,3,5(10)-triene to give 3-methoxy-16β,17β-dihydro-4′H-[1,3]-oxazino[5′,6′: 16,17]estra-1,3,5(10)-triene derivatives. Under similar conditions 3-methoxy-16α, 17α-dihydro-4′H-oxeto[3′,2′:16,17]estra-1,3,5(10)-triene undergoes a Wagner-Meerwein rearrangement.

Original languageEnglish
Pages (from-to)1613-1622
Number of pages10
JournalCollection of Czechoslovak Chemical Communications
Volume63
Issue number10
Publication statusPublished - Oct 1998

Fingerprint

Oxazines
Nitriles
Ether
Steroids
Derivatives
tetrafluoroboric acid
oxetane

Keywords

  • Dihydrooxazines
  • Oxetanes
  • Ring expansions
  • Ritter reaction
  • Steroids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

One-step conversion of oxetane-fused to 1,3-oxazine-fused steroids. / Hajnal, Andrea; Wölfling, J.; Schneider, G.

In: Collection of Czechoslovak Chemical Communications, Vol. 63, No. 10, 10.1998, p. 1613-1622.

Research output: Contribution to journalArticle

@article{9a3ed21a223c451ca5ed94393f06e5fd,
title = "One-step conversion of oxetane-fused to 1,3-oxazine-fused steroids",
abstract = "In a ring-expansion reaction, alkyl and aryl nitriles, in the presence of tetrafluoroboric acid-diethyl ether complex, react with 3-methoxy-16β,17β-dihydro-4′H-oxeto[3′,2′:16,17] estra-1,3,5(10)-triene to give 3-methoxy-16β,17β-dihydro-4′H-[1,3]-oxazino[5′,6′: 16,17]estra-1,3,5(10)-triene derivatives. Under similar conditions 3-methoxy-16α, 17α-dihydro-4′H-oxeto[3′,2′:16,17]estra-1,3,5(10)-triene undergoes a Wagner-Meerwein rearrangement.",
keywords = "Dihydrooxazines, Oxetanes, Ring expansions, Ritter reaction, Steroids",
author = "Andrea Hajnal and J. W{\"o}lfling and G. Schneider",
year = "1998",
month = "10",
language = "English",
volume = "63",
pages = "1613--1622",
journal = "ChemPlusChem",
issn = "2192-6506",
publisher = "Wiley-VCH Verlag",
number = "10",

}

TY - JOUR

T1 - One-step conversion of oxetane-fused to 1,3-oxazine-fused steroids

AU - Hajnal, Andrea

AU - Wölfling, J.

AU - Schneider, G.

PY - 1998/10

Y1 - 1998/10

N2 - In a ring-expansion reaction, alkyl and aryl nitriles, in the presence of tetrafluoroboric acid-diethyl ether complex, react with 3-methoxy-16β,17β-dihydro-4′H-oxeto[3′,2′:16,17] estra-1,3,5(10)-triene to give 3-methoxy-16β,17β-dihydro-4′H-[1,3]-oxazino[5′,6′: 16,17]estra-1,3,5(10)-triene derivatives. Under similar conditions 3-methoxy-16α, 17α-dihydro-4′H-oxeto[3′,2′:16,17]estra-1,3,5(10)-triene undergoes a Wagner-Meerwein rearrangement.

AB - In a ring-expansion reaction, alkyl and aryl nitriles, in the presence of tetrafluoroboric acid-diethyl ether complex, react with 3-methoxy-16β,17β-dihydro-4′H-oxeto[3′,2′:16,17] estra-1,3,5(10)-triene to give 3-methoxy-16β,17β-dihydro-4′H-[1,3]-oxazino[5′,6′: 16,17]estra-1,3,5(10)-triene derivatives. Under similar conditions 3-methoxy-16α, 17α-dihydro-4′H-oxeto[3′,2′:16,17]estra-1,3,5(10)-triene undergoes a Wagner-Meerwein rearrangement.

KW - Dihydrooxazines

KW - Oxetanes

KW - Ring expansions

KW - Ritter reaction

KW - Steroids

UR - http://www.scopus.com/inward/record.url?scp=0041351995&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0041351995&partnerID=8YFLogxK

M3 - Article

VL - 63

SP - 1613

EP - 1622

JO - ChemPlusChem

JF - ChemPlusChem

SN - 2192-6506

IS - 10

ER -