Preparation of New Nitrogen-Bridged Heterocycles. 43. Synthesis and Reaction of 5aH-Pyrido[1,2-d][1,3,4]thiadiazepine Derivatives

• Published in: Journal of organic chemistry Vol. 62; no. 22; pp. 7788 - 7793
• Main Authors: Kakehi, Akikazu, Ito, Suketaka, Ishida, Fumihito, Tominaga, Yoshinori
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 31.10.1997; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo971066o

Reactions of some 1-pyridinio- and 1-(4-methylpyridinio)(arenethiocarbonyl)amidates with dimethyl acetylenedicarboxylate in chloroform afforded neither the expected dimethyl 2-aryl-5aH-pyrido[1,2-d][1,3,4]thiadiazepine-4,5-dicarboxylates nor their intramolecular Diels−Alder adducts, but gave novel rearranged products, dimethyl 4-aryl-5-thia-2,3-diazatricyclo[4.3.2.02,7]undeca-3,8,10-triene-6,11-dicarboxylates in low to moderate yields. On the other hand, similar reactions of 1-(3-methylpyridinio)- and 1-(2-methylquinolinio)(arenethiocarbonyl)amidates with the same reagent provided 1:1 primary adducts, dimethyl 2-aryl-6-methyl-5aH-pyrido[1,2-d][1,3,4]thiadiazepine-4,5-dicarboxylates and dimethyl 2-aryl-5a-methyl-5aH-[1,3,4]thiadiazepino[4,5-a]quinoline-4,5-dicarboxylates, respectively.