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Features And Applications Of Reactions Of α,β-unsaturated N-acylbenzotriazoles With Amino Compounds
X. Wang, Zhifang Li, Xiangming Zhu, H. Mao, Xuefei Zou, L. Kong, X. Li
Published 2008 · Chemistry
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Abstract Promoted by triethylamine, α,β-unsaturated N-acylbenzotriazoles reacted with amino compounds in a variety of ways. Thus, N-cinnamoylbenzotriazoles reacting with aromatic amines afforded novel addition products β-benzotriazolyl amides 3, which might be normally formed from the alternative but unknown 1,4-addition of benzotriazole to N-cinnamoylamides. The type 3 compounds could also result from the reaction between N-crotonoylbenzotriazole and aliphatic amines. However, normal 1,4-addition could occur between α,β-unsaturated aliphatic N-acylbenzotriazoles and aromatic amines, leading to β-amino N-acylbenzotriazoles 4 in good yields. In addition, exclusive 1,2-addition of aliphatic amines to N-cinnamoylbenzotriazoles gave excellent yields of cinnamides 5. Accordingly, three possible routes were proposed to rationalize the formation of compounds 3–5. Finally, with o-phenylenediamine and o-aminothiophenol as the substrates, the 1,4- and 1,2-addition to α,β-unsaturated N-acylbenzotriazoles could take place concurrently and the corresponding heterocycles 1,5-benzodiazepine-2-one and 1,5-benzothiazepine-4-one were constructed, respectively.
This paper references
A rational approach to the design and synthesis of a new bradykinin B(1) receptor antagonist.
P. Bedos (2000)
Synthesis of β-methyl-β-alanine-l-proline-XAA tripeptides by Yb(OTf)3 catalysed Michael addition of amines to N-crotonyl-l-proline-XAA: a versatile route to cyclic β-methyl-β-alanine-derived tripeptides via ring closing metathesis
B. Saha (2002)
A Catalytic Enantioselective Aza‐Michael Reaction: Novel Protocols for Asymmetric Synthesis of β‐Amino Carbonyl Compounds
L. Xu (2005)
Ketene-ketenimine rearrangements in the gas phase and in polar media. 1,3-Migration intermediates and sequential transition states.
J. Finnerty (2005)
Conjugated additions of amines and β-amino alcohols to trifluorocrotonic acid derivatives: synthesis of ψ[NHCH(CF3)]-retro-thiorphan
M. Molteni (2007)
A Facile Synthesis of Substituted Benzodiazepines Using Solid Support
M. Kidwai (2004)
An Efficient Synthesis of α,β-Unsaturated Thiol Esters
X. Wang (2006)
Significant rate acceleration of the aza-Michael reaction in water
B. Ranu (2007)
LiClO4 Accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions
N. Azizi (2004)
Boric acid: a novel and safe catalyst for aza-Michael reactions in water
M. K. Chaudhuri (2005)
Chemoselective, accelerated and stereoselective aza-Michael addition of amines to N-phenylmaleimide by using TMEDA based receptors
Yuefeng Bi (2004)
Synthesis of β-amino esters via aza-michael addition of amines to alkenes promoted on silica: A useful and recyclable surface
B. Basu (2004)
Cu(acac)2 Immobilized in Ionic Liquids: A Recoverable and Reusable Catalytic System for Aza‐Michael Reactions
M. Kantam (2005)
Cerium(IV) ammonium nitrate (CAN) catalyzed aza-Michael addition of amines to α,β-unsaturated electrophiles
Zheng Duan (2006)
Bromodimethylsulfonium bromide mediated Michael addition of amines to electron deficient alkenes
A. Khan (2007)
Recent advances in the stereoselective synthesis of β-amino acids
M. Liu (2002)
A green, ionic liquid and quaternary ammonium salt-catalyzed aza-Michael reaction of α,β-ethylenic compounds with amines in water
L. Xu (2004)
Efficient Conversion of Carboxylic Acids into N-Acylbenzotriazoles
A. R. Katritzky (2003)
Conjugate Addition Reactions in Organic Synthesis
P. Perlmutter (1992)
Ni(II) complexes containing chiral tridentate phosphines as new catalysts for the hydroamination of activated olefins.
L. Fadini (2003)
γ,δ-Unsaturated β-Diketones by Acylation of Ketones
A. Katritzky (2005)
Sequential one-pot InBr(3)-catalyzed 1,4- then 1,2-nucleophilic addition to enones.
M. Bandini (2002)
Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters
G. Bartoli (1994)
1,2- vs 1,4-Addition of Acylbenzotriazoles to α,β-Unsaturated Aldehydes and Ketones. A Novel Route to 3-Alkyl-4,6-diaryl-3,4-dihydropyran-2-ones
A. Katritzky (2002)
Enantioselective addition of amines to alkenoyl-N-oxazolidinones
Kelin Li (2005)
Aza-Michael reactions catalyzed by samarium diiodide
I. Reboule (2005)
Efficient microwave access to polysubstituted amidines from imidoylbenzotriazoles.
A. Katritzky (2006)
Aryliminopropadienone-C-Amidoketenimine- Amidinoketene-2-Aminoquinolone Cascades and the Ynamine-Isocyanate Reaction.
C. Wentrup (1999)
Stereoselective addition of 2-aminothiophenol to α-alkoxycinnamic acid derivatives---alternative synthesis of (±)-diltiazem---
O. Miyata (1993)
Asymmetric aza-Michael reactions catalyzed by cinchona alkaloids.
D. Perdicchia (2007)
Highly regioselective Friedel–Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles
Xuefei Zou (2006)
Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3.7H2O/NaI system supported on alumina in solvent-free conditions.
G. Bartoli (2005)
Conjugate Addition of Amines to α,β-Enones Promoted by CeCl3·7H2O−NaI System Supported in Silica Gel
G. Bartoli (2001)
Michael Additions of Benzotriazole-Stabilized Carbanions. A Review
A. Katritzky (1998)
One-pot synthesis of cinnamoyl hydrazides
A. R. Katritzky (2001)
Highly Enantioselective Catalytic Conjugate Addition of N‐Heterocycles to α,β‐Unsaturated Ketones and Imides
M. Gandelman (2005)
Dicationic [(BINAP)Pd(solvent)2]2+[TfO-]2: enantioselective hydroamination catalyst for alkenoyl-N-oxazolidinones.
Kelin Li (2003)
Asymmetric synthesis of beta-amino esters by aza-Michael reaction of alpha,beta-unsaturated amides using (S,S)-(+)-pseudoephedrine as chiral auxiliary.
Juan Etxebarria (2004)
ZrOCl2·8H2O on montmorillonite K10 accelerated conjugate addition of amines to α,β-unsaturated alkenes under solvent-free conditions
M. M. Hashemi (2006)
The ionic liquid ethyltri-n-butylphosphonium tosylate as solvent for the acid-catalysed hetero-Michael reaction
Nazira Karodia (2006)
Enantioselective synthesis of .beta.-amino esters through high pressure-induced addition of amines to .alpha.,.beta.-ethylenic esters
J. D'angelo (1986)
Reaction kinetics of cinnamoyl, .beta.-2-furylacryloyl, and .beta.-2-thienylacryloyl chlorides with anilines in benzene
G. Alberghina (1978)
Efficient Syntheses of β-Amino-N-acylbenzotriazoles and Cinnamides through Regioselective 1,4- or 1,2-Addition of Amines to N-Cinnamoylbenzotriazoles
X. Wang (2005)
Stereoselective Syntheses of Spicy Components in Peppers
A. Ohta (1991)
Alkyl, unsaturated, (hetero)aryl, and N-protected alpha-amino ketones by acylation of organometallic reagents.
A. Katritzky (2006)
Highly efficient KF/Al2O3-catalyzed versatile hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles to α,β-ethylenic compounds
L. Yang (2005)
Retro-Ene Reactions in Acylallene Derivatives.
H. Bibas (1998)
One-step assembly of carbamoyl-substituted heteroannelated [1,4]thiazepines.
Alexey P. Ilyn (2006)
Bismuth nitrate-catalyzed versatile Michael reactions.
N. Srivastava (2003)
Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations.
B. Narasimhan (2004)
(S,S)-(+)-pseudoephedrine as chiral auxiliary in asymmetric aza-Michael reactions. Unexpected selectivity change when manipulating the structure of the auxiliary.
Juan Etxebarria (2005)
Highly efficient aza-Michael reactions of aromatic amines and N-heterocycles catalyzed by a basic ionic liquid under solvent-free conditions
Lei Yang (2006)
Asymmetric synthesis of ß-amino acids and α-substituted β-amino acids
G. Cardillo (1996)
Enantioselective aza-Michael reactions catalyzed by samarium iodobinaphtholate
I. Reboule (2005)
Acylbenzotriazoles as Advantageous N-, C-, S-, and O-Acylating Agents
A. R. Katritzky (2005)
The Analgesic Activity of N,N-Dialkyl Amides1
D. Papa (1950)
N-Acylbenzotriazoles: neutral acylating reagents for the preparation of primary, secondary, and tertiary amides
M. Katritzky (2000)
One‐Pot Tandem 1,4–1,2‐Addition of Phosphites to α,β‐Unsaturated Imines for the Synthesis of Glutamic Acid Analogues
K. Moonen (2005)
Borax as an Efficient Metal‐Free Catalyst for Hetero‐Michael Reactions in an Aqueous Medium
S. Hussain (2007)
Oxazepines and thiazepines. Part 10: Synthesis of carboxylic acid derivatives of 2,3-dihydro-2-phenyl-1,5-benzothiazepin-4(5H)-ones
A. Lévai (1980)
Ketene-Ketene Rearrangement: Substituent Effects on the 1,3-Migration in .alpha.-Oxo Ketenes
M. W. Wong (1994)
Synthesis of a 10,000 member 1,5-benzodiazepine-2-one library by the directed sorting method.
T. F. Herpin (2000)
A Convenient One-Pot Synthesis of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones
V. Ambrogi (1987)
β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water
K. Surendra (2006)
Enantioselective Synthesis ofβ-Amino Sulfones by aza-Michael Addition to Alkenyl Sulfones
D. Enders (1999)
Partition coefficients of some N-alkyl- and N,N-dialkyl-derivatives of some cinnamamides and benzalcyanoacetamides in the system cyclohexane–water
A. Delaney (1969)
This paper is referenced by
Palladacycle catalyzed asymmetric P-H addition of diarylphosphines to N-enoyl phthalimides.
Renta Jonathan Chew (2014)
SmI3-Catalyzed Addition of Amines to α,β-Unsaturated N-Acylbenzotriazoles
X. Wang (2009)
Our Odyssey with Functionalized Chiral Phosphines: From Optical Resolution to Asymmetric Synthesis to Catalysis.
Renta Jonathan Chew (2016)
Formal [3 + 4] Annulation of α,β-Unsaturated Acyl Azoliums: Access to Enantioenriched N-H-Free 1,5-Benzothiazepines.
Chao Fang (2017)
Base and catalyst-free synthesis of nitrobenzodiazepines via a cascade N-nitroallylation-intramolecular aza-Michael addition involving o-phenylenediamines and nitroallylic acetates
Divya K. Nair (2019)
Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands
Sergey E. Lyubimov (2017)
Preparation of Fe-Ni/C Composite Catalyst for the Hydrazine Hydrate Catalytic Reduction
Jin Hua Zhou (2013)
Chapter 7: Seven-Membered Rings
Adam G. Meyer (2009)
Peptide–Heterocycle Chimera: New Classes of More Drug-Like Peptidomimetics by Ligations of Peptide–Bis(electrophiles) with Various Bis(nucleophiles)
A. El-Dahshan (2011)
Enantioselective synthesis of 4-substituted 4,5-dihydro-1H-[1,5]benzodiazepin-2(3H)-ones by the Lewis base-catalyzed hydrosilylation.
X. Chen (2011)
Regioselective addition of thiophenol to α,β-unsaturated N-acylbenzotriazoles
Ziming Xia (2011)
Ecofriendly and efficient procedure for hetero-Michael addition reactions with an acidic ionic liquid as catalyst and reaction medium
Minoo Dabiri (2011)
Preparation, Reactivity, and Synthetic Utility of Simple Benzotriazole Derivatives
Romaric Gérardy (2015)
Direct and Enantioselective Synthesis of N-H-Free 1,5-Benzodiazepin-2-ones by an N-Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction.
Chao Fang (2018)
Synthesis of heterocycles mediated by benzotriazole. 1. Monocyclic systems.
A. Katritzky (2010)
First Highly Enantioselective Synthesis of Benzodiazepinones by Catalytic Hydrogenation
M. Rueping (2010)
Michael Addition Reaction Catalyzed by Imidazolium Chloride to Protect Amino Groups and Construct Medium Ring Heterocycles
Zeshu Dai (2019)
Features and Applications of Reactions of α,β-Unsaturated N-Acylbenzotriazoles with Amino Compounds.
X. Wang (2008)