Synthesis, structure and some reactions of 4a',5′,6′,7′,8′,8a'-hexahydro-4′H-spiro[cyclohexane-1,9′-[1,2,4]triazolo[5,1-b]-quinazolines]

✍ Scribed by Victor M. Chernyshev; Dmitry A. Khoroshkin; Andrey N. Sokolov; Vitaly A. Taranushich; Eugene S. Gladkov; Svetlana V. Shishkina; Oleg V. Shishkin; Sergey M. Desenko

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2008
• Tongue: English
• Weight: 674 KB
• Volume: 45
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570450527

✦ Synopsis

Abstract

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2′‐Substituted 5′,6′,7′,8′‐tetrahydro‐4′H‐spiro[cyclohexane‐1,9′‐[1,2,4]triazolo[5,1‐b]quinazolines] 3a‐d were synthesized by condensation of 3‐substituted 5‐amino‐1,2,4‐triazoles 1a‐d with 2‐cyclohexylidene cyclohexanone 2 in DMF. The compounds 3 were hydrogenated with sodium borohydride in ethanol to give 2′‐substituted cis‐4a',5′,6′,7′,8′,8a'‐hexahydro‐4′H‐spiro[cyclohexane‐1,9′‐[1,2,4]triazolo[5,1‐b]quinazolines] 4a‐d in high yields. The reactions of alkylation, acylation and sulfonylation of the compounds 4 were studied. The structure of the synthesized compounds was determined on the basis of NMR measurements including HSQC, HMBC, NOESY techniques and confirmed by the X‐ray analysis of 6 and 11b. The described synthetic protocols provide rapid access to novel and diversely substituted hydrogenated [1,2,4]triazolo[5,1‐b]quinazolines.