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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]
Author(s) -
Chernyshev Victor M.,
Khoroshkin Dmitry A.,
Sokolov Andrey N.,
Taranushich Vitaly A.,
Gladkov Eugene S.,
Shishkina Svetlana V.,
Shishkin Oleg V.,
Desenko Sergey M.
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450527
Subject(s) - chemistry , cyclohexanone , cyclohexane , sodium borohydride , alkylation , acylation , stereochemistry , medicinal chemistry , organic chemistry , catalysis
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.