Synthesis 2016; 48(24): 4495-4508
DOI: 10.1055/s-0036-1588588
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Fluorinated Multisubstituted Pyrimidines and 1,5-Benzodiazepines via Fluorinated N,S-Acetals

Nutan Sharma
a   Organic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India
,
Tejpal Singh Chundawat
b   Department of Applied Sciences, The NorthCap University (formerly ITM University), Gurgaon-122017, Haryana, India   Email: sunitabhagat28@gmail.com
,
Subash Chandra Mohapatra
a   Organic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India
,
Sunita Bhagat*
a   Organic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India
› Author Affiliations
Further Information

Publication History

Received: 22 April 2016

Accepted after revision: 08 August 2016

Publication Date:
09 September 2016 (online)


Abstract

An efficient and novel approach using highly versatile but less exploited monofluorinated α-oxoketene N,S-acetals as synthons for the synthesis of novel fluorinated multisubstituted pyrimidines and 1,5-benzodiazepines by cyclization with guanidine nitrate and o-phenylenediamine, respectively, has been developed. The synthesized compounds, which carry additional functional groups that allow further functionalization, are of considerable interest as building blocks in medicinal chemistry. X-ray crystallographic studies confirmed the formation of the desired cyclized product.

Supporting Information

 
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