Poster Presentation at the Week of Undergraduate Excellence at Drexel on May 17th 2018
Anisyl Sulfanyl Methyl IsoCyanide (ASMIC): Rapid Construction of Heterocyclic Scaffolds
To make heterocycles in one pot
And functionalize them is what we sought
Heterocycles are found in almost everything
They have atoms other than carbon also present in the ring
Heterocycles are found in small molecule drugs and even caffeine
Also in our DNA’s adenine, thymine, Guanine and cytosine
Formic acid, thiol, formaldehyde and formamide
Together form anisyl sulfanyl methyl formamide
From the product, POCl3 removes a water molecule
to make ASMIC while we keep it at -10° C cool
We then make different heterocycles from ASMIC
At first n-Butyl Lithium does a proton pick
Carbanion formed attacks on an electrophile
Like a ketone, ester or even a nitrile
Forming a ring like oxazole or imidazole
Making 5 membered heterocycles, we reach half the goal
The ring has carbon and nitrogen from isocyanide
and carbons from the electrophile on their either side
proton on the C is something we can exchange
based on choice, with an alkyl group range
Ring has oxygen or nitrogen based on the electrophile
Making the heterocycle very versatile
However, sulphur anisyl handle was hard to cleave
so we oxidized it to sulfoxide, which is happier to leave
When t-Butyl lithium is added to sulfoxide
Lone pair on Sulphur attacks on benzyl bromide
Now the Sulphur has 10 electrons around
And five ligands that are bound
This sulfurane ligand coupling is too hard
With other organoLithium and Grignard
The big t-Butyl group we propose
Forces the oxazole and benzyl ligand close
So it can easily undergo reductive elimination
A new carbon carbon bond creation.
Anisyl Sulfanyl Methyl IsoCyanide (ASMIC): Rapid Construction of Heterocyclic Scaffolds
To make heterocycles in one pot
And functionalize them is what we sought
Heterocycles are found in almost everything
They have atoms other than carbon also present in the ring
Heterocycles are found in small molecule drugs and even caffeine
Also in our DNA’s adenine, thymine, Guanine and cytosine
Formic acid, thiol, formaldehyde and formamide
Together form anisyl sulfanyl methyl formamide
From the product, POCl3 removes a water molecule
to make ASMIC while we keep it at -10° C cool
We then make different heterocycles from ASMIC
At first n-Butyl Lithium does a proton pick
Carbanion formed attacks on an electrophile
Like a ketone, ester or even a nitrile
Forming a ring like oxazole or imidazole
Making 5 membered heterocycles, we reach half the goal
The ring has carbon and nitrogen from isocyanide
and carbons from the electrophile on their either side
proton on the C is something we can exchange
based on choice, with an alkyl group range
Ring has oxygen or nitrogen based on the electrophile
Making the heterocycle very versatile
However, sulphur anisyl handle was hard to cleave
so we oxidized it to sulfoxide, which is happier to leave
When t-Butyl lithium is added to sulfoxide
Lone pair on Sulphur attacks on benzyl bromide
Now the Sulphur has 10 electrons around
And five ligands that are bound
This sulfurane ligand coupling is too hard
With other organoLithium and Grignard
The big t-Butyl group we propose
Forces the oxazole and benzyl ligand close
So it can easily undergo reductive elimination
A new carbon carbon bond creation.