The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4

被引：1

作者：

Khoroshunova, Yulia V. ^{[1
,2
]}

Morozov, Denis A. ^{[1
]}

Taratayko, Andrey I. ^{[1
,2
]}

Dobrynin, Sergey A. ^{[1
]}

Eltsov, Ilia V. ^{[2
]}

Rybalova, Tatyana V. ^{[1
]}

Sotnikova, Yulia S. ^{[1
]}

Polovyanenko, Dmitriy N. ^{[1
]}

Asanbaeva, Nargiz B. ^{[1
,2
]}

Kirilyuk, Igor A. ^{[1
]}

机构：

[1] RAS, SB, NN Vorozhtsov Inst Organ Chem, Academician Lavrentiev Ave 9, Novosibirsk 630090, Russia

[2] Novosibirsk State Univ, Dept Nat Sci, Pirogova Str 1, Novosibirsk 630090, Russia

来源：

MOLECULES | 2021年 / 26卷 / 19期

关键词：

appel reaction; alkylation; nitroxide; azepane; Hofmann elimination; CYCLOADDITION; PRECURSORS; NITROXIDES;

D O I：

10.3390/molecules26196000

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Activation of a hydroxyl group towards nucleophilic substitution via reaction with methanesulfonyl 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 (X = O center dot; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahydro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocyclopenta[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.

引用

页数：17

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