Preparation of New Nitrogen-Bridged Heterocycles. 43.1 Synthesis and Reaction of 5aH-Pyrido[1,2-d][1,3,4]thiadiazepine Derivatives

Autor:	and Fumihito Ishida, Yoshinori Tominaga, Akikazu Kakehi, Suketaka Ito
Rok vydání:	1997
Předmět:	Dimethyl acetylenedicarboxylate chemistry.chemical_compound Chloroform Primary (chemistry) chemistry Intramolecular force Reagent Organic Chemistry Polymer chemistry chemistry.chemical_element Nitrogen Adduct D-1
Zdroj:	The Journal of Organic Chemistry. 62:7788-7793
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo971066o
Popis:	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.
Databáze:	OpenAIRE
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