A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero–Diels–Alder reaction

Shinde Vidyacharan; A. Sagar; Duddu S. Sharada

doi:10.1039/c5ob01023c

A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero–Diels–Alder reaction

Organic & Biomolecular Chemistry ◽

10.1039/c5ob01023c ◽

2015 ◽

Vol 13 (28) ◽

pp. 7614-7618 ◽

Cited By ~ 19

Author(s):

Shinde Vidyacharan ◽

A. Sagar ◽

Duddu S. Sharada

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

First Time

A new route has been developed for the synthesis of 4-aminoquinoline drug like moleculesviaaza hetero–Diels–Alder reaction starting from 2H-indazole as a diene for the first time.

Download Full-text

Ring-Closing Metathesis Approach to Cage Propellanes Containing Oxepane and Tetrahydrofuran Hybrid System

Synthesis ◽

10.1055/s-0036-1591726 ◽

2017 ◽

Vol 49 (24) ◽

pp. 5339-5350 ◽

Cited By ~ 15

Author(s):

Sambasivarao Kotha ◽

Subba Cheekatla ◽

Darshan Mhatre

Keyword(s):

Claisen Rearrangement ◽

Alder Reaction ◽

Diels Alder ◽

Ring Closing Metathesis ◽

Cage Compounds ◽

Transannular Cyclization ◽

Diels Alder Reaction ◽

Grignard Addition ◽

Key Steps ◽

First Time

The preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult to prepare by traditional methods. The synthetic sequence described here opens up new routes to higher order polycycles containing heteroatoms without the involvement of protecting groups. Transannular cyclization observed during Grignard addition and the RCM protocol used here may be applicable to generate unknown oxygenated cage systems.

Download Full-text

Two-dimensional Raman correlation spectroscopy reveals molecular structural changes during temperature-induced self-healing in polymers based on the Diels–Alder reaction

Physical Chemistry Chemical Physics ◽

10.1039/c5cp02151k ◽

2015 ◽

Vol 17 (35) ◽

pp. 22587-22595 ◽

Cited By ~ 26

Author(s):

R. Geitner ◽

J. Kötteritzsch ◽

M. Siegmann ◽

T. W. Bocklitz ◽

M. D. Hager ◽

...

Keyword(s):

Correlation Analysis ◽

Structural Changes ◽

Alder Reaction ◽

Diels Alder ◽

Correlation Spectroscopy ◽

Self Healing ◽

Two Dimensional ◽

Diels Alder Reaction ◽

First Time ◽

Raman Correlation Spectroscopy

For the first time two-dimensional Raman correlation analysis has been used to study self-healing polymers based on the Diels–Alder reaction.

Download Full-text

Thiourea-catalyzed Diels–Alder reaction of a naphthoquinone monoketal dienophile

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.9.158 ◽

2013 ◽

Vol 9 ◽

pp. 1414-1418 ◽

Cited By ~ 3

Author(s):

Carsten S Kramer ◽

Stefan Bräse

Keyword(s):

Natural Products ◽

Total Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Selective Synthesis ◽

Quaternary Center ◽

Diels Alder Reaction ◽

Cycloaddition Product ◽

Sterically Hindered ◽

First Time

A variety of organocatalysts were screened for the catalysis of the naphthoquinone monoketal Diels–Alder reaction. In this study we found that Schreiner's thiourea catalyst 10 and Jacobson's thiourea catalyst 12 facilitate the cycloaddition of the sterically hindered naphthoquinone monoketal dienophile 3 with diene 4. The use of thiourea catalysis allowed for the first time the highly selective synthesis of the exo-product 2a in up to 63% yield. In this reaction a new quaternary center was built. The so formed cycloaddition product 2a represents the ABC tricycle of beticolin 0 (1) and is also a valuable model substrate for the total synthesis of related natural products.

Download Full-text

Imino Diels–Alder reaction — An efficient synthetic protocol for 2-methyl-4-substituted tetrahydroquinolines catalyzed by copper dipyridine dichloride

Canadian Journal of Chemistry ◽

10.1139/v10-016 ◽

2010 ◽

Vol 88 (5) ◽

pp. 443-452 ◽

Cited By ~ 9

Author(s):

C. S. Kavitha ◽

K. M. Hosamani ◽

R. S. Harisha

Keyword(s):

Elemental Analysis ◽

Alder Reaction ◽

Diels Alder ◽

Reusable Catalyst ◽

Substituted Anilines ◽

H Nmr ◽

Diels Alder Reaction ◽

First Time ◽

C Nmr

For the first time, copper dipyridine dichloride (CuPy2Cl2) is used as an efficient and reusable catalyst for the imino Diels–Alder reaction of para-substituted anilines with N-vinylpyrrolidinone, N-vinylcarbazole, and N-vinylcaprolactam in acetonitrile to afford the corresponding 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives in excellent yields with good purity. The products were characterized by FTIR, 1H NMR, 13C NMR, MS, and elemental analysis.

Download Full-text

Construction of sulfur-containing compounds with anti-cancer stem cell activity using thioacrolein derived from garlic based on nature-inspired scaffolds

Organic & Biomolecular Chemistry ◽

10.1039/d1ob01992a ◽

2022 ◽

Author(s):

Taichi Yoneda ◽

Naoto Kojima ◽

Takahiro Matsumoto ◽

Daisuke Imahori ◽

Tomoe Ohta ◽

...

Keyword(s):

Stem Cell ◽

Cell Activity ◽

Alder Reaction ◽

Diels Alder ◽

Diels Alder Reaction ◽

Anti Cancer ◽

Stem Cell Activity ◽

First Time ◽

Sulfur Containing ◽

Sulfur Containing Compounds

We reported for the first time that thioacroleinproduced by allicin, a major component in garlic, undergoes the regioselective sequential double Diels–Alder reaction.

Download Full-text

Homogeneous Zinc(II) Catalysis in Accelerated Vulcanization III. Degradation Modes of Mono- and Disulfidic Cross-Links

Rubber Chemistry and Technology ◽

10.5254/1.3538792 ◽

1999 ◽

Vol 72 (1) ◽

pp. 27-42 ◽

Cited By ~ 3

Author(s):

P. J. Nieuwenhuizen ◽

J. M. van Veen ◽

J. G. Haasnoot ◽

J. Reedijk

Keyword(s):

Direct Evidence ◽

Alder Reaction ◽

Diels Alder ◽

Molecular Processes ◽

Cross Link ◽

Hydride Shift ◽

Diels Alder Reaction ◽

New Information ◽

Cross Links ◽

First Time

Abstract This paper reports a Reaction-Stage-Modeling study dealing with degradation of mono- and disulfidic cross-links, providing new information about the molecular processes underlying the macrophysical phenomenon of reversion. The monosulfidic model cross-link (2,3-dimethyl-2-buten-1-yl)(2,3-dimethyl-1-buten-3-yl)sulfide was found to degrade at a relatively low temperature of 140 °C to yield olefins and α, β-unsaturated thioaldehydes. The latter species are not stable enough to be observed directly, but instead dimerize via an auto-Diels-Alder reaction to give a—fully-characterized—1,3-dithiin. The disulfidic model cross-link bis(2,3-dimethyl-2-buten-1-yl)disulfide was observed to degrade according to a previously unknown mechanism, involving a 1,4-hydride shift, to furnish a 1,3-dipolar intermediate. The reaction is catalyzed by bis(diethyldithiocarbamato)zinc(II), ZDEC, and the activation enthalpy ΔH‡ of the reaction has been determined to be ∼ 71(7) kJ mol− . Several dienophiles and dipolarophiles were applied to trap the α, β-unsaturated thioaldehyde and 1,3-dipolar intermediate, but neither was successful. Overall, this study has furnished direct evidence for degradation of mono- and disulfidic cross-links via hydrogen shifts and indicates, for the first time, in what way zinc complexes may cause cross-link degradation and induce reversion in rubber vulcanizates.

Download Full-text

A flexible approach to the synthesis of type II and III lepadin alkaloids

Synthesis ◽

10.1055/a-1681-4067 ◽

2021 ◽

Author(s):

Yue Hu ◽

He Gu ◽

Yuanliang Jia ◽

Guiyin Luo ◽

Xiaochuan Chen

Keyword(s):

Alder Reaction ◽

Diels Alder ◽

Piperidine Ring ◽

Type Ii ◽

Flexible Approach ◽

Type Iii ◽

Diels Alder Reaction ◽

First Time

A flexible approach to both the type II and III lepadin alkaloids is developed for the first time. A key Diels−Alder reaction based on a novel chiral ketolactone dienophile is employed to obtain the desirable all-cis-trisubstituted cyclohexene with excellent regio- and stereoselectivity. As the subsequent closure of the piperidine ring is devised at the N1 and C2 position via a intramolecular nucleophilic amination, the two stereochemical types of lepadin frameworks with the opposite configuration at C2 can be conveniently accessible from a common intermediate. By the approach, lepadins D, E (type II) and F (type III) are stereoselectively synthesized from ethyl L-lactate.

Download Full-text

Studies on the transannular Diels–Alder reaction of 15-membered macrocyclic trienes containing a trans-trans diene. Part II: Evidence for unsymmetrical transition states in the formation of A.B.C.[6.6.7] tricyclic products

Canadian Journal of Chemistry ◽

10.1139/v95-208 ◽

1995 ◽

Vol 73 (10) ◽

pp. 1695-1710 ◽

Cited By ~ 3

Author(s):

Dennis G. Hall ◽

Renate Müller ◽

Pierre Deslongchamps

Keyword(s):

Lewis Acids ◽

Transition States ◽

Preceding Paper ◽

Alder Reaction ◽

Membered Ring ◽

Diels Alder ◽

Proximity Effects ◽

Diels Alder Reaction ◽

Stereocontrolled Synthesis ◽

First Time

In the preceding paper (Part I) we described the preparation of 10 model TTT and TTC cyclopentadecatrienes. Their conversion to A.B.C.[6.6.7] tricyclic products via a transannular Diels–Alder (TADA) reaction and the analysis of the resulting diastereoselection along with proofs of structures are described in the present article (Part II). The required temperature of reaction was significantly higher (~100 °C) in comparison to that required for the 14-membered lower homologs, indicating that proximity effects are playing a key role in the TADA reaction. The presence of ester groups in the chain was found to favor either of the two possible transition states (endo or exo) on the basis of steric effects, thus controlling the TST/CSC ratio of tricycles from TTC macrocycles, and the TAC/CAT ratio from TTT macrocycles. A formyl substituent on the dienophile can further influence the diastereoselection through the hypothesis of unsymmetrical transition states and allowed, for the first time, the use of Lewis acids as catalysts in the TADA reaction. This investigation demonstrates a general methodology for the stereocontrolled synthesis of A.B.C.[6.6.7] tricycle structures related to several polycyclic natural products. Keywords: transannular, Diels–Alder, 15-membered ring, A.B.C.[6.6.7] tricycles, diterpene.

Download Full-text