Bifunctionalized linked bis-spiro[furo[2,3-d]pyrimidine6,5 -pyrimidine]2,2 ,4,4 ,6 (3H ,3 H ,5H)-pentaones derived from one-pot reaction of (thio)barbituric acids with aromatic dialdehydes and BrCN in the presence of Et3N

Nader NOROOZI PESYAN; Mohammad JALILZADEH

doi:https://doi.org/10.3906/tar-1211-9

Article Details

Bifunctionalized linked bis-spiro[furo[2,3-d]pyrimidine6,5 -pyrimidine]2,2 ,4,4 ,6 (3H ,3 H ,5H)-pentaones derived from one-pot reaction of (thio)barbituric acids with aromatic dialdehydes and BrCN in the presence of Et3N

Authors:

Nader NOROOZI PESYAN | Mohammad JALILZADEH

Publisher:

TUBITAK

Main Topics:

Chemistry and allied sciences

Journal:

Turkish Journal of Chemistry 2012 Vol.36 Issue 6, pp.788-804

Document Type:

Article

Publication Date:

5/2012

Document Language:

English

Document ID (Org No.):

2000727512

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/tar-1211-9

Abstract:

 

Reaction of pyrimidine-(1H,3H,5H)-2,4,6-trione (barbituric  acid), 1,3-dimethyl pyrimidine-(1H,3H,5H)-2,4,6-trione (1,3-dimethyl  barbituric acid), and 1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-  dione (1,3-diethyl thiobarbituric acid) with cyanogen bromide and  aromatic dialdehydes in the presence of triethylamine leads to the  selective and efficient formation of a novel class of bifunctionalized  stable heterocyclic bis-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]  2,2',4,4',6'(3H,3'H,5H)pentaones and their sulfur analogues, which are  dimeric forms of barbiturate linked by a phenyl ring.  A proposed  mechanism was suggested for the formation of the products.  The  reaction of phthalaldehyde with BrCN and (thio)barbituric acids  resulted in only monofunctionalized spiro[furo[2,3-d]pyrimidine-6,5'-  pyrimidine]2,2',4,4',6'(3H,3'H,5H)pentaones, while isophthalaldehyde  and terphthalaldehyde resulted in the bifunctionalized form.

 

Reaction of pyrimidine-(1H,3H,5H)-2,4,6-trione (barbituric  acid), 1,3-dimethyl pyrimidine-(1H,3H,5H)-2,4,6-trione (1,3-dimethyl  barbituric acid), and 1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-  dione (1,3-diethyl thiobarbituric acid) with cyanogen bromide and  aromatic dialdehydes in the presence of triethylamine leads to the  selective and efficient formation of a novel class of bifunctionalized  stable heterocyclic bis-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]  2,2',4,4',6'(3H,3'H,5H)pentaones and their sulfur analogues, which are  dimeric forms of barbiturate linked by a phenyl ring.  A proposed  mechanism was suggested for the formation of the products.  The  reaction of phthalaldehyde with BrCN and (thio)barbituric acids  resulted in only monofunctionalized spiro[furo[2,3-d]pyrimidine-6,5'-  pyrimidine]2,2',4,4',6'(3H,3'H,5H)pentaones, while isophthalaldehyde  and terphthalaldehyde resulted in the bifunctionalized form.

Article Details

Bifunctionalized linked bis-spiro[furo[2,3-d]pyrimidine6,5 -pyrimidine]2,2 ,4,4 ,6 (3H ,3 H ,5H)-pentaones derived from one-pot reaction of (thio)barbituric acids with aromatic dialdehydes and BrCN in the presence of Et3N

Authors: Nader NOROOZI PESYAN | Mohammad JALILZADEH

Publisher: TUBITAK

Main Topics: Chemistry and allied sciences

Journal: Turkish Journal of Chemistry 2012 Vol.36 Issue 6, pp.788-804

Document Type: Article

Publication Date: 5/2012

Document Language: English

Document ID (Org No.): 2000727512

Frequency: Bimonthly

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/tar-1211-9

Issues

Authors:

Nader NOROOZI PESYAN | Mohammad JALILZADEH

Publisher:

TUBITAK

Main Topics:

Chemistry and allied sciences

Journal:

Turkish Journal of Chemistry 2012 Vol.36 Issue 6, pp.788-804

Document Type:

Article

Publication Date:

5/2012

Document Language:

English

Document ID (Org No.):

2000727512

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/tar-1211-9