Issue 24, 2012
From the journal:

RSC Advances

A carbanion induced ring switching synthesis of spiranes: an unprecedented approach†

Hardesh K. Maurya,ae   Ramendra Pratap,c   Abhinav Kumar,‡a   Brijesh Kumar,b   Volker Huch,d   Vishnu K. Tandon*a  and  Vishnu Ji Ram*a  

* Corresponding authors

a Department of Chemistry, Lucknow University, Lucknow, India
E-mail: vjiram@yahoo.com (VJR), hardesh11@yahoo.co.in (HKM), vishnutandon@yahoo.co.in (VKT)
Fax: 91 522 2623405
Tel: +91 522 2960779

b Division of SAIF, Central Drug Research Institute, Lucknow, India

c Department of Chemistry, University of Delhi, North Campus, Delhi, India

d Institute of Inorganic Chemistry, University of Saarland, Saarbrucken, Germany

e Medicinal Chemistry Department, Central Institute of Medicinal and aromatic Plants, PO. CIMAP, Kukrail Road, Lucknow, India

Abstract

An unique approach to the synthesis of heterocyclic spiranes through ring switching transformation of suitably functionalized 2H-pyran-2-ones, benzo[h]chromene and thiochromeno[4,3-b]pyrans has been developed. The spirane dimer 11d displayed interesting halogen-hydrogen bonding to generate an elliptical cavity and may be relevant to the generation of a host guest assembly for specific cations and also a low helimerization energy barrier of spirane 17a.

Graphical abstract: A carbanion induced ring switching synthesis of spiranes: an unprecedented approach

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Article information

DOI
https://doi.org/10.1039/C2RA21587J
Article type
Paper
Submitted
27 Jul 2012
Accepted
30 Jul 2012
First published
31 Jul 2012

RSC Adv., 2012,2, 9091-9099

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A carbanion induced ring switching synthesis of spiranes: an unprecedented approach

H. K. Maurya, R. Pratap, A. Kumar, B. Kumar, V. Huch, V. K. Tandon and V. Ji Ram, RSC Adv., 2012, 2, 9091 DOI: 10.1039/C2RA21587J

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