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]

Abstract

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.

Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds

“…It should be noted that for similar treatments involving 3-amino-1,2,4-triazole [7,29–30] the structures of the final products were different depending on whether a multicomponent or sequential procedure was used, while in our case both procedures gave the same compounds.…”

Divergent On-DNA Transformations from DNA-Linked Piperidones

“…4-Aminopiperidine and its derivatives are common structural motifs in approved drugs for various diseases, such as hypersensitivity (mizolastine), digestive diseases (prucalopride, cinitapride, and cisapride), nerve diseases (remifentanil and tetrabenazine), and cardiovascular disease (indoramin) (Figure ). Meanwhile, fused [1,2,4]­triazolo­[1,5- a ]­pyrimidine compounds exhibit antihypertensive activity and act as antagonists of adenosine and nociceptin receptors . Fused quinoline rings are also common structural motifs found in natural and synthetic derivatives with interesting physiological properties, such as antimalarial, antiasthmatic, antihypertensive, and antibacterial activities.…”

Synthesis of Partially Saturated Tetrazolocyclopyrimidines their Oxidation Izologues

“…Работа выполнена при финансовой поддержке Российского фонда фундаментальных исследований (проект № 13-03-00318). Соединения, сочетающие в своей структуре тетразольный и пиримидиновый фрагменты, обладают широким спектром биологической активности [1][2][3][4][5]. В последние годы внимание исследователей привлекают азолоцикланопиримидины различной степени насыщенности в связи с возможностью изучения влияния размера алицикла, степени насыщенности, конформационных особенностей на их реакционную способность, фармакологическую активность и проявление иных практически полезных свойств.…”