Reactions of Azetidines | Ambeed

Reactions of Azetidines

Reactions of Azetidines

Oxetane and azetidine exhibit significantly lower reactivity compared to their three-membered counterparts, yet they still undergo analogous ring-opening reactions.

Reacion-1:

Concentrated hydrochloric acid causes azetidine to open when heated.

Related Products:

A7355672231673-10-098%

2,2-Dimethylazetidin-3-ol hydrochloride

A123787942308-06-795%

3-(Methoxymethyl)azetidine hydrochloride

A592433791614-73-898%

(S)-2-(Fluoromethyl)azetidine hydrochloride

A302528102624-96-498%

Azetidine-3-carboxylic acid hydrochloride

A133003148644-09-197%

3-Methoxyazetidine hydrochloride

A1494361356114-40-398%

Azetidin-3-yl acetate 2,2,2-trifluoroacetate

A3348271357923-33-195%

2-(Azetidin-3-yl)propan-2-ol hydrochloride

A17739591188-13-597%

tert-Butyl azetidin-3-ylcarbamate

A129531217806-26-397%

tert-Butyl azetidin-3-ylcarbamate hydrochloride

A1698437729-30-895%

(R)-Azetidine-2-carboxylic acid

A6891871221272-90-796%

3-(Trifluoromethyl)azetidine hydrochloride

A333480897019-55-598%

3-Propoxyazetidine hydrochloride

A681923791614-71-698%

(R)-2-Methylazetidine hydrochloride

A244686162698-26-295%

Methyl azetidine-2-carboxylate hydrochloride

A3385802173991-98-398%

tert-Butyl 2-(azetidin-3-yl)acetate hydrochloride

A247103313468-63-298%

3-Chloroazetidine hydrochloride

A1469072227199-20-297%

(2S,3S)-2-Methylazetidin-3-ol hydrochloride

A11295253871-08-297%

tert-Butyl azetidine-3-carboxylate hydrochloride

A155815321890-22-697%

1-(Azetidin-3-yl)-N,N-dimethylmethanamine dihydrochloride

A7507661205750-03-397%

3-Ethylazetidine-3-carbonitrile hydrochloride

A465827935670-07-898%

N,N-Dimethylazetidin-3-amine hydrochloride

A322876905843-93-898%

3-Methoxy-3-methylazetidine hydrochloride

A460990936909-11-498%

3-Methylazetidine-3-carbonitrile

A445112229496-83-795%

3-Bromoazetidine hydrobromide

A10811971909337-74-195%

3-Ethylazetidine 2,2,2-trifluoroacetate

A8206461354792-76-995%

3-(Difluoromethyl)azetidine hydrochloride

A13362145347-82-898%

A176693124668-46-897%

3-Methylazetidin-3-ol hydrochloride

A131842470666-35-497%

(2S,4S)-2,4-Dimethylazetidine hydrochloride

A177185250274-91-095%

Azetidin-2-ylmethanol

A5669211170905-43-798%

tert-Butyl (2-(azetidin-3-yl)ethyl)carbamate hydrochloride

A106141221095-80-397%

Azetidin-3-ylmethanamine dihydrochloride

A164465104587-62-497%

(S)-Azetidin-2-ylmethanol

A7977251088884-71-295%

2,2-Dimethylazetidine hydrochloride

A112367535924-73-397%

3-Ethoxyazetidine hydrochloride

A536513503-29-798%

A6171182231674-32-998%

3-(Trifluoromethyl)azetidin-3-amine dihydrochloride

A144836647854-72-697%

(R)-Azetidine-2-carboxylic acid hydrochloride

A32490689381-03-397%

3,3-Dimethylazetidine hydrochloride

A1306161187929-81-295%

tert-Butyl (azetidin-3-ylmethyl)carbamate oxalate

A172992935669-28-695%

3-Methylazetidine hydrochloride

A147240345954-83-897%

Azetidine-3-carbonitrile hydrochloride

A147280209329-11-398%

(R)-Azetidin-2-ylmethanol

A168654405090-31-597%

Ethyl azetidine-3-carboxylate hydrochloride

A8415212231664-90-598%

(2R,3R)-2-Methylazetidin-3-ol hydrochloride

A479252935668-82-995%

(R)-2-(Methoxymethyl)azetidine

A51405336476-78-597%

Azetidine-3-carboxylic acid

A354265100202-39-997%

Methyl azetidine-3-carboxylate hydrochloride

A575813864248-69-198%

N-Methylazetidine-3-carboxamide hydrochloride

A141778928038-44-297%

Azetidin-3-ylmethanol hydrochloride

A133986943060-59-195%

tert-Butyl azetidin-3-yl(methyl)carbamate hydrochloride

A8332672231676-11-097%

N-Ethyl-N-methylazetidin-3-amine dihydrochloride

A2175692517-04-698%

Azetidine-2-carboxylic acid

A543812288315-03-797%

3,3-Difluoroazetidine hydrochloride

A977971935669-67-398%

(S)-2-Methylazetidine hydrochloride

A2376691170108-38-997%

tert-Butyl (azetidin-3-ylmethyl)carbamate hydrochloride

A373741256931-54-198%

3-Methylazetidin-3-ol

A10235718621-18-697%

Azetidin-3-ol hydrochloride

A145279617718-46-497%

3-Fluoroazetidine hydrochloride

A1047561820683-31-598%

3-(Methanesulfonylmethyl)azetidine hydrochloride

A7355672231673-10-098%

2,2-Dimethylazetidin-3-ol hydrochloride

A123787942308-06-795%

3-(Methoxymethyl)azetidine hydrochloride

A592433791614-73-898%

(S)-2-(Fluoromethyl)azetidine hydrochloride

A302528102624-96-498%

Azetidine-3-carboxylic acid hydrochloride

A133003148644-09-197%

3-Methoxyazetidine hydrochloride

A1494361356114-40-398%

Azetidin-3-yl acetate 2,2,2-trifluoroacetate

A3348271357923-33-195%

2-(Azetidin-3-yl)propan-2-ol hydrochloride

A17739591188-13-597%

tert-Butyl azetidin-3-ylcarbamate

A129531217806-26-397%

tert-Butyl azetidin-3-ylcarbamate hydrochloride

A1698437729-30-895%

(R)-Azetidine-2-carboxylic acid

A6891871221272-90-796%

3-(Trifluoromethyl)azetidine hydrochloride

A333480897019-55-598%

3-Propoxyazetidine hydrochloride

Reacion-2:

Nucleophiles readily react with azetidinium ions.

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A11457541418274-28-899%

2-(3-(2-Chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)-3-hydroxyazetidin-1-yl)isonicotinic acid

A244686162698-26-295%

Methyl azetidine-2-carboxylate hydrochloride

A284893255882-72-597%

Methyl 1-Boc-azetidine-2-carboxylate

A5369011260593-39-298%

(R)-1-tert-Butyl 2-methyl azetidine-1,2-dicarboxylate

A12738818085-37-597%

Methyl 1-benzylazetidine-2-carboxylate

A27763187791-58-097%

Benzyl 4-oxoazetidine-2-carboxylate

A2940181203683-75-395%

3-(4-(Trifluoromethyl)phenyl)azetidine hydrochloride

A3232981203681-52-098%

tert-Butyl 3-(4-bromophenyl)azetidine-1-carboxylate

A1485477606-30-697%

3-Phenylazetidine hydrochloride

A17113394268-29-895%

4-(Azetidin-3-yl)benzonitrile hydrochloride

A196563883901-62-097%

tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate

A9925321240970-70-095%

tert-Butyl 3-(4-(methoxycarbonyl)phenyl)azetidine-1-carboxylate

A115352550370-15-597%

3-Phenylazetidin-3-ol hydrochloride

A1943166N/A98%

(3-(1-(tert-Butoxycarbonyl)azetidin-3-yl)phenyl)boronic acid

A10998832059972-24-495%

tert-Butyl 5'-bromo-1',2'-dihydrospiro[azetidine-3,3'-indole]-1-carboxylate

A1684561398609-80-797%

tert-Butyl 5'-bromo-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

A4508297215-23-895%

3,3-Diphenylazetidine

A619400913814-30-998%

1-Benzhydryl-3-phenylazetidine

A12166831533438-83-398%

4-(1-(5-(4,5-Dimethyl-1H-pyrazol-3-yl)-2,4-dimethylbenzoyl)azetidin-3-yl)benzonitrile

A11778272097262-60-598+%

4-(1-(5-(3,4-Dimethyl-1H-pyrazol-5-yl)-2,4-dimethylbenzoyl)azetidin-3-yl)benzonitrile

A11457541418274-28-899%

2-(3-(2-Chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)-3-hydroxyazetidin-1-yl)isonicotinic acid

A244686162698-26-295%

Methyl azetidine-2-carboxylate hydrochloride

A284893255882-72-597%

Methyl 1-Boc-azetidine-2-carboxylate

A5369011260593-39-298%

(R)-1-tert-Butyl 2-methyl azetidine-1,2-dicarboxylate

A12738818085-37-597%

Methyl 1-benzylazetidine-2-carboxylate

A27763187791-58-097%

Benzyl 4-oxoazetidine-2-carboxylate

A2940181203683-75-395%

3-(4-(Trifluoromethyl)phenyl)azetidine hydrochloride

A3232981203681-52-098%

tert-Butyl 3-(4-bromophenyl)azetidine-1-carboxylate

A1485477606-30-697%

3-Phenylazetidine hydrochloride

A17113394268-29-895%

4-(Azetidin-3-yl)benzonitrile hydrochloride

A196563883901-62-097%

tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate

A9925321240970-70-095%

tert-Butyl 3-(4-(methoxycarbonyl)phenyl)azetidine-1-carboxylate

Reacion-3:

An azetidine's reaction with a chloroformate can yield either the dealkylated heterocycle or the ring-opened product (γ-chloroamine).

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tert-Butyl 3-(aminomethyl)-3-methylazetidine-1-carboxylate

A74654826687-49-098%

1-Methyl-3-azetidinol Hydrochloride

A4032311008526-70-295%

tert-Butyl 3-hydroxy-3-(nitromethyl)azetidine-1-carboxylate

A1489381064194-10-097%

tert-Butyl 3-bromoazetidine-1-carboxylate

A1879591257293-79-098%

tert-Butyl 3-(2-hydroxypropan-2-yl)azetidine-1-carboxylate

A13288482682097-49-897%

(S)-(1-Methylazetidin-2-yl)methanamine dihydrochloride

A17132451077-14-697%

(S)-1-(tert-Butoxycarbonyl)azetidine-2-carboxylic acid

A473361158602-43-898%

tert-Butyl 3-(3-hydroxypropyl)azetidine-1-carboxylate

A2416801255666-59-198+%

tert-Butyl 3,3-difluoroazetidine-1-carboxylate

A356165325775-44-897%

tert-Butyl 3-(aminomethyl)azetidine-1-carboxylate

A3043291262411-27-795%

tert-Butyl 3-amino-3-(hydroxymethyl)azetidine-1-carboxylate

A162774161511-85-997%

(S)-1-Boc-2-Azetidinemethanol

A8683962750139-24-195%

(1-(tert-Butoxycarbonyl)azetidin-3-yl)boronic acid

A604151174346-82-898%

tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate

A813329228868-28-895%

(S)-tert-Butyl 2-(cyanomethyl)azetidine-1-carboxylate

A189343141699-55-098%

tert-Butyl 3-hydroxyazetidine-1-carboxylate

A535638820971-67-398%

tert-Butyl 3-[methoxy(methyl)carbamoyl]azetidine-1-carboxylate

A119262161511-90-698%

(R)-1-Boc-2-Azetidinemethanol

A114103105443-94-595%

(S)-tert-Butyl 2-carbamoylazetidine-1-carboxylate

A27727763177-41-395%

1-(Azetidin-1-yl)-2-chloroethanone

A495801959238-28-995%

1-Isopropylazetidine-3-carboxylic acid

A1273351126650-67-698%

1-(tert-Butoxycarbonyl)-3-fluoroazetidine-3-carboxylic acid

A5820221255666-44-498%

tert-Butyl 3-fluoroazetidine-1-carboxylate

A1069111443983-86-597%

2-(3-(Fluoromethyl)azetidin-1-yl)ethan-1-ol

A63903213156-04-295%

1-tert-Butyl-3-azetidinol

A224035941585-25-798%

tert-Butyl 3-mercaptoazetidine-1-carboxylate

A220437610791-05-497%

Methyl 1-Boc-azetidine-3-carboxylate

A8363652007919-81-397%

tert-Butyl 3-bromo-3-(hydroxymethyl)azetidine-1-carboxylate

A454215141699-58-398%

1-Boc-3-Methanesulfonyloxyazetidine

A151931870089-49-995%

tert-Butyl 3-acetylazetidine-1-carboxylate

A101835142253-57-498%

(1-(tert-Butoxycarbonyl)azetidin-3-yl)methyl methanesulfonate

A2864271346674-10-997%

1-tert-Butyl 3-ethyl azetidine-1,3-dicarboxylate

A4459071955515-46-498%

1-Ethylazetidin-3-amine dihydrochloride

A7596601340301-52-198%

1-Propylazetidin-3-ol

A269179497160-14-297%

tert-Butyl 3-(2-methoxy-2-oxoethyl)azetidine-1-carboxylate

A5560332055839-99-997%

tert-Butyl 3-amino-3-carbamoylazetidine-1-carboxylate hydrochloride

A12508562682096-96-297%

(S)-(1-Methylazetidin-2-yl)methanamine hydrochloride

A7952071788041-57-598+%

tert-Butyl 3-cyano-3-fluoroazetidine-1-carboxylate

A226506147621-21-497%

tert-Butyl azetidine-1-carboxylate

A603132887591-62-097%

1-(tert-Butoxycarbonyl)-3-methylazetidine-3-carboxylic acid

A349320254454-54-197%

tert-Butyl 3-iodoazetidine-1-carboxylate

A220489429669-07-897%

1-Boc-3-(methoxy)azetidine

A231796398489-36-698%

tert-Butyl 3-hydroxy-3-propylazetidine-1-carboxylate

A111414228857-58-797%

(R)-1-(tert-Butoxycarbonyl)azetidine-2-carboxylic acid

A4536381462921-50-198%

1-(3-Aminoazetidin-1-yl)ethanone hydrochloride

A575213887588-82-197%

tert-Butyl 2-cyanoazetidine-1-carboxylate

A4778261803609-11-198%

1-(1-methylazetidin-3-yl)methanamine dihydrochloride

A1325281445951-55-297%

tert-Butyl 3-nitroazetidine-1-carboxylate

A8044681466514-89-597%

2-Bromo-1-(3-fluoro-3-methylazetidin-1-yl)ethan-1-one

A6491321056166-09-698%

(R)-tert-Butyl 2-(2-hydroxyethyl)azetidine-1-carboxylate

A7714431493737-08-898%

tert-butyl 3-cyano-3-hydroxyazetidine-1-carboxylate

A600214253176-94-298%

N-Boc-3-(iodomethyl)azetidine

A8769691146951-82-795%

tert-Butyl 3-(2-hydroxyethoxy)azetidine-1-carboxylate

A348795177947-96-597%

tert-Butyl 3-formylazetidine-1-carboxylate

A8922511648864-55-495%

tert-Butyl 3-((2-hydroxyethyl)sulfonyl)azetidine-1-carboxylate

A1412751420859-80-895%

tert-Butyl 3-(2-bromoethyl)azetidine-1-carboxylate

A1218371422344-49-797%

2-(1-(tert-Butoxycarbonyl)-3-methylazetidin-3-yl)acetic acid

A13740367896-18-895%

2-(Azetidin-1-yl)ethanol

A503471898271-20-095%

1-Boc-(3-Aminoethyl)azetidine

A2238221430219-73-098%

Potassium (1-(tert-butoxycarbonyl)azetidin-3-yl)trifluoroborate

A5900281158758-85-098%

tert-Butyl 3-(aminomethyl)-3-methylazetidine-1-carboxylate

A74654826687-49-098%

1-Methyl-3-azetidinol Hydrochloride

A4032311008526-70-295%

tert-Butyl 3-hydroxy-3-(nitromethyl)azetidine-1-carboxylate

A1489381064194-10-097%

tert-Butyl 3-bromoazetidine-1-carboxylate

A1879591257293-79-098%

tert-Butyl 3-(2-hydroxypropan-2-yl)azetidine-1-carboxylate

A13288482682097-49-897%

(S)-(1-Methylazetidin-2-yl)methanamine dihydrochloride

A17132451077-14-697%

(S)-1-(tert-Butoxycarbonyl)azetidine-2-carboxylic acid

A473361158602-43-898%

tert-Butyl 3-(3-hydroxypropyl)azetidine-1-carboxylate

A2416801255666-59-198+%

tert-Butyl 3,3-difluoroazetidine-1-carboxylate

A356165325775-44-897%

tert-Butyl 3-(aminomethyl)azetidine-1-carboxylate

A3043291262411-27-795%

tert-Butyl 3-amino-3-(hydroxymethyl)azetidine-1-carboxylate

A162774161511-85-997%

(S)-1-Boc-2-Azetidinemethanol

See also:

Azetidine Derivatives in Drug Design >

References:

[1]Antermite D, Degennaro L, Luisi R. Recent advances in the chemistry of metallated azetidines[J]. Organic & Biomolecular Chemistry, 2017, 15(1): 34-50.

[2]Reidl T W, Anderson L L. Divergent Functionalizations of Azetidines and Unsaturated Azetidines[J]. Asian Journal of Organic Chemistry, 2019, 8(7): 931-945.

[3]Couty F, Evano G. Azetidines: new tools for the synthesis of nitrogen heterocycles[J]. Synlett, 2009, 2009(19): 3053-3064.