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

Nutan Sharma; Tejpal Singh Chundawat; Subash Chandra Mohapatra; Sunita Bhagat

doi:10.1055/s-0036-1588588

Synthesis, Table of Contents

Synthesis 2016; 48(24): 4495-4508
DOI: 10.1055/s-0036-1588588

paper

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

Nutan Sharma

^aOrganic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India

,

Tejpal Singh Chundawat

^bDepartment of Applied Sciences, The NorthCap University (formerly ITM University), Gurgaon-122017, Haryana, India Email: sunitabhagat28@gmail.com

,

Subash Chandra Mohapatra

^aOrganic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India

,

Sunita Bhagat*

^aOrganic Synthesis Research Laboratory, Department of Chemistry, A.R.S.D. College, University of Delhi, New Delhi-110021, India

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Abstract

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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.

Key words

fluorinated compounds - ketene acetals - pyrimidines - benzodiazepines - binucleophiles

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