Tetrahedron Letters p. 4486 - 4489 (2010)
Update date:2022-08-03
Topics:
Qin, Lan-Ying
Cole, Andrew G.
Metzger, Axel
Brescia, Marc-Raleigh
Saionz, Kurt W.
Zhang, Joan J.
Rigollier, Pascal
Wareing, James R.
Gstach, Hubert
Zimmermann, Juerg
Dolle, Roland E.
Baldwin, John J.
Henderson, Ian
A facile synthesis of novel 2-amino-6-arylmethyl-7-carboxamido-7,8- dihydropyrimido[5,4-f][1,4]thiazepin-5-ones is described. The synthesis was developed on solid phase and was applied to provide a series of analogs in good yield. The key reactions are acylation of a cysteine derivative with 2,4-dichloropyrimidine-5-carbonyl chloride followed by cyclization to generate a 6-arylmethyl-7-carboxamido-2-chloro-7,8-dihydropyrimido[5,4-f][1,4]thiazepin-5- one, which is further derivatized with an amine to give the desired 2-amino-6-arylmethyl-7-carboxamido-7,8-dihydropyrimido[5,4-f][1,4] thiazepin-5-one.
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