Synthesis and reactions of 2-chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes

Reim, Stefanie; Adeel, Muhammad; Hussain, Ibrar; Yawer, Mirza Arfan; Ahmed, Zafar; Villinger, Alexander; Langer, Peter

doi:10.1016/j.tetlet.2008.05.151

Cited by 13 publications

(11 citation statements)

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“…[27,28] We have re-cently reported the synthesis of 4-chlorophenols by cyclization of 1,3-bis(silyloxy)buta-1,3-dienes with 2-chloro-3-silyloxy-2-en-1-ones [29] and the synthesis of chlorinated heteroand carbacycles through cyclization reactions of 2-chloro-1,3-bis(silyloxy)buta-1,3-dienes. [30] Recently we have reported [31] the synthesis of the first 4-chloro-1,3-bis(silyloxy)-buta-1,3-dienes and their application to the synthesis of chlorinated arenes and hetarenes. Here we report full details and a significant extension of the scope.…”

Section: Introductionmentioning

confidence: 99%

Diversity‐Oriented Synthesis of Chlorinated Arenes by One‐Pot Cyclizations of 4‐Chloro‐1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes

et al. 2009

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A variety of 3‐chlorosalicylates were prepared by one‐potcyclizations of the first reported 4‐chloro‐1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes with various 1,3‐dielectrophiles. These include cyclizations with 3‐silyloxy‐2‐en‐1‐ones, 3‐aryl‐3‐silyloxy‐2‐en‐1‐ones, 1‐methoxy‐1‐en‐3‐ones, 1,1‐bis(methylthio)‐1‐en‐3‐ones, 3‐oxo orthoesters, 1,1,3,3‐tetraethoxypropanes, 1,1‐diacetylcyclopropane, and 3‐formylchromones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Introductionmentioning

confidence: 99%

Diversity‐Oriented Synthesis of Chlorinated Arenes by One‐Pot Cyclizations of 4‐Chloro‐1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes

et al. 2009

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“…The corresponding 2-chloro-1-alkoxy-1,3-bis(silyloxy)-1,3-butadienes 3a-c were prepared by deprotonation (with use of lithium diisopropylamide, LDA) of 2a-c at -78 °C and slow addition of trimethylchlorosilane. 32 The chloride functionality proved to be compatible with the reaction conditions (Scheme 1).…”

Section: Cyclizations Of 2-chloro-13-bis(trimethylsilyloxy)-13-butadienesmentioning

confidence: 87%

“…silyloxy-and 3-alkoxy-2-en-1-ones, 27 iminium salts, 28 benzopyrylium triflates, 29 and various other electrophiles. [30][31][32] In this context, we have also studied the use of chlorinated systems and the present article provides an account with respect to the synthesis of chlorinated arenes and hetarenes starting from 1,3-bis(trimethylsilyloxy)-1,3-butadienes.…”

Section: Account Syn Lettmentioning

confidence: 99%

“…Compounds 7a,b are not selectively available by direct halogenation and other synthetic procedures of the corresponding homophthalate, because of limitations such as the formation of regioisomeric mixtures and poor selectivities. [32][33][34] Scheme 3 Synthesis of homophthalates 7a and 7b. Reagents and reaction conditions:…”

Section: 4-dihydroxy-homophthalatesmentioning

confidence: 99%

“…This reaction was applied to chlorinated diene 3b to afford chlorine-containing 2-(arylsulfonyl)pyridine 9 (Scheme 4). [32][33][34]…”

Section: -(Arylsulfonyl)chloropyridinesmentioning

confidence: 99%

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Synthesis of Chlorinated Arenes and Hetarenes by One-Pot Cyclizations of 1,3-Bis-silyl Enol Ethers

Hassan

Langer

2019

Synlett

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This account describes our recent findings and progress in synthesizing chlorinated arenes and hetarenes by one-pot cyclizations of 1,3-bis-silyl enol ether derivatives. These reactions allow for the preparation of highly functionalized products with a high level of regioselectivity. The synthetic routes are cost-effective avoiding additional functionalization steps. The products are difficult to be accessed by other methods. The chlorine atom is of relevance in medicinal and agriculture chemistry. In addition, it allows further functionalizations by transition-metal-catalyzed cross-coupling reactions.1 Introduction2 Cyclizations of 2-Chloro-1,3-bis(silyloxy)-1,3-butadienes2.1 3,5-Dihydroxychlorophthalates2.2 2,4-Dihydroxy-homochlorophthalates2.3 2-(Arylsulfonyl)chloropyridines2.4 1-Azaxanthones3 Cyclizations of 4-Chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes3.1 3-Chlorosalicylates3.2 Functionalized Chlorobiaryls3.3 3-Chloro-5-(2-chloroethyl)-salicylates3.4 2,4-Dihydroxychlorobenzophenones4 Cyclizations of 2-Chloro-3-(silyloxy)-2-en-1-ones4.1 Functionalized Chlorophenols4.2 Functionalized Chlorinated Biaryls and Chlorofluorenones4.3 Functionalized Chlorochromenones4.4 Functionalized 3-(Methylthio)chlorophenols4.5 Functionalized 3-Chloromethylphenols5 Conclusions6 List of Abbreviations

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ChemInform Abstract: Synthesis and Reactions of 2‐Chloro‐1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes.

et al. 2008

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2008Halogenated alcohols P 0120 Synthesis and Reactions of 2-Chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes.-The synthesis of E/Z-isomeric mixtures of 1,3-bis(siloxy)-1,3-butadienes (IV) and (XVIII) is described and their reaction with a variety of carbon electrophiles is studied. -(REIM, S.; ADEEL, M.; HUSSAIN, I.; YAWER, M. A.; AHMED, Z.; VILLINGER, A.; LANGER*, P.; Tetrahedron Lett. 49 (2008) 33, 4901-4904; Inst. Chem., Univ. Rostock, D-18059 Rostock, Germany; Eng.) -Mais 46-059

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Synthesis and reactions of 2-chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes

Cited by 13 publications

References 25 publications

Diversity‐Oriented Synthesis of Chlorinated Arenes by One‐Pot Cyclizations of 4‐Chloro‐1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes

Diversity‐Oriented Synthesis of Chlorinated Arenes by One‐Pot Cyclizations of 4‐Chloro‐1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes

Synthesis of Chlorinated Arenes and Hetarenes by One-Pot Cyclizations of 1,3-Bis-silyl Enol Ethers

ChemInform Abstract: Synthesis and Reactions of 2‐Chloro‐1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes.

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