Efficient synthesis of pyrimido[1,2-c] [1,3]benzothiazin-6-imines and related tricyclic heterocycles by S(N)Ar-type C-S, C-N, or C-O bond formation with heterocumulenes.
A simple and practical synthetic method of pyrimido[1,2-c][1,3]benzothiazin-6-imines and related tricyclic heterocycles has been developed. Treatment of 2-(2-haloaryl)tetrahydropyrimidines with NaH and a heterocumulene such as carbon disulfide, isothiocyanates, and isocyanates in DMF provides the desired cyclization products through a regioselective S(N)Ar-type reaction. This method provides direct access to PD 404182 and related compounds.
Mizuhara
Tsukasa
T
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Oishi
Shinya
S
Fujii
Nobutaka
N
Ohno
Hiroaki
H
D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*; D013843:Thiazines / Q000138:chemical synthesis*
D006575:Heterocyclic Compounds, 3-Ring; D007097:Imines; D011090:Polyenes; D013843:Thiazines; D013455:Sulfur; D009584:Nitrogen; D010100:Oxygen