A Concise Synthesis of Pyrimidinophanes from 6-Aryl-5-Cyano-2-Thiouracil

A convenient synthesis of 2,3- and 2,4-pyrimidinophanes (3,5,6) has been described from 6-aryl-5-cyano-2-thiouracils (1a-c). A reaction of 2-thiouracil with dibromomethane produced 2a-c, which on further interaction with dihaloalkane under basic condition produced 2,3-pyrimidinophanes (3a,b). Haloge...

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Bibliographic Details
Published in:Journal of chemical research 2003-06, Vol.2003 (6), p.380-382
Main Authors: Upadhyay, D N, Agarwal, Nidhi, Goel, Atul, Ram, Vishnu Ji
Format: Article
Language:English
Subjects:
Halogenation
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Summary:A convenient synthesis of 2,3- and 2,4-pyrimidinophanes (3,5,6) has been described from 6-aryl-5-cyano-2-thiouracils (1a-c). A reaction of 2-thiouracil with dibromomethane produced 2a-c, which on further interaction with dihaloalkane under basic condition produced 2,3-pyrimidinophanes (3a,b). Halogenation of 2a,c with POCl3 led to yield respective chloropyrimidines (4a,b), which on further reaction with diaminoalkane and 1,4-phenylenediamine separately yielded 2,4-pyrimidinophanes (5a-d and 6a,b).
ISSN:1747-5198
2047-6507
DOI:10.3184/030823403103174227