The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4 Full article
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Molecules
, E-ISSN: 1420-3049 |
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| Output data | Year: 2021, Volume: 26, Number: 19, Article number : 6000, Pages count : DOI: 10.3390/molecules26196000 | ||||
| Tags | Alkylation; Appel reaction; Azepane; Hofmann elimination; Nitroxide | ||||
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Abstract:
Activation of a hydroxyl group towards nucleophilic substitution via reaction with me-thanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes 1a–d (Х = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahy-dro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocy-clopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
Cite:
Khoroshunova Y.V.
, Morozov D.A.
, Taratayko A.I.
, Dobrynin S.A.
, Eltsov I.V.
, Rybalova T.V.
, Sotnikova Y.S.
, Polovyanenko D.N.
, Asanbaeva N.B.
, Kirilyuk I.A.
The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4
Molecules. 2021. V.26. N19. 6000 . DOI: 10.3390/molecules26196000 WOS Scopus OpenAlex
The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4
Molecules. 2021. V.26. N19. 6000 . DOI: 10.3390/molecules26196000 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000707772900001 |
| Scopus: | 2-s2.0-85116594968 |
| OpenAlex: | W3202874250 |