Novel synthesis of 2,2-dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans

Huang, Po‐Jung Jimmy; Cameron, T. Stanley; Jha, Amitabh

doi:10.1016/j.tetlet.2008.10.083

Cited by 27 publications

(10 citation statements)

References 32 publications

(27 reference statements)

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“…Subsequently, we substantiated this mechanistic pathway by developing a pTSA catalyzed four-component reaction involving 2-naphthol, paraformaldehyde, isobutyraldehyde, and morpholine (1 molar equivalent each) under microwave conditions identical to the original three component reaction [58]. This indeed led to formation of 73 (R 0 ¼ ¼R"¼ ¼Me, ANR 2 ¼ ¼morpholine) and 74 (ANR 2 ¼ ¼morpholine) in 52% and 43% yields, respectively (Scheme 32).…”

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 88%

“…Our research group is also actively engaged in exploitation of 2-naphthol and 2-tetralone analogs to produce novel molecular frameworks [52][53][54][55][56][57][58]. Our efforts have also led to synthesis of three kinds of 2,3-dihydro-1H-naphtho [2,1-b]pyrans [56][57][58].…”

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 99%

“…Our efforts have also led to synthesis of three kinds of 2,3-dihydro-1H-naphtho [2,1-b]pyrans [56][57][58]. Reaction between 2-tetralone and substituted ortho-hydroxy aromatic aldehydes under acidic conditions resulted in formation of benzene-fused 2,3-dihydro-1H-naphtho[2,1-b]pyrans or 12H-benzo[a]xanthenes (67, Scheme 27) in moderate to excellent yields (55-94%) [56].…”

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 99%

“…In another endeavor, we developed a microwaveassisted synthesis of 3-(dialklamino)-2,2-dialkyl-1,2-dihydro-naphtho[2,1-b]pyrans (73) [58]. These series of compounds were formed in moderate to good yields (45-72%) from 2-naphthol, a secondary amine, and 3-hydroxy-2,2-dialkylpropanaldehydes (69) in presence of catalytic amount of p-toluenesulfonic acid using focused microwave radiation as energy source (Scheme 30).…”

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 99%

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Synthetic approaches to 3H‐naphtho[2,1‐b]pyrans and 2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans

Jha

Huang

2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Naphtho [2,1-b]pyran nuclei are prevalent in natural products with significant biological and medicinal properties. 3,3-Disubstituted 3H-naphtho[2,1-b]pyrans are photochromic and find use in electronic display systems, ophthalmic lenses, optical switches, and temporary or permanent memories. Of the various possible structural isomers of naphthopyran framework, this review is an account of reported synthetic procedures to produce 3H-naphtho[2,1-b]pyrans and their dihydro analogs, 2,3-dihydro-1H-naphtho[2,1-b]pyrans. The advantages and disadvantages of each procedure in terms of yields, complexity, formation of side-products, use of uncommon/expensive reagents, etc., are also described.

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Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 88%

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 99%

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 99%

Section: Methods Of Synthesis Of 23-dihydro-1h-naphtho[21-b]pyransmentioning

confidence: 99%

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Synthetic approaches to 3H‐naphtho[2,1‐b]pyrans and 2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans

Jha

Huang

2009

Journal of Heterocyclic Chem

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“…Starting from 2-naphthol, 2,2-disubstituted 3-hydroxypropanals and cyclic secondary amines, Jha et al achieved the synthesis of 2,2-dialkyl-3-dialkylamino-2,3-dihydro-1 H -naphtho[2,1- b ]pyrans under solvent-free conditions using p TSA as catalyst [75]. It is important to note, that during the reaction, 2,2-disubstituted 3-hydroxypropanals 26 decompose to formaldehyde and 2,2-disubstituted acetaldehydes 28 .…”

Section: Reviewmentioning

confidence: 99%

Mannich base-connected syntheses mediated by ortho-quinone methides

Barta¹,

Fülöp²,

Szatmári³

2018

Beilstein J. Org. Chem.

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This article provides an overview about specifically modified Mannich reactions where the process involves an ortho-quinone methide (o-QM) intermediate. The reactions are classified on the basis of the o-QM source followed by the reactant, e.g., the dienophile partner in cycloaddition reactions (C=C or C=N dienophiles) or by the formation of multicomponent Mannich adducts. Due to the important pharmacological activities of these reactive o-QM intermediates, special attention is paid to the biological activity of these compounds.

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ChemInform Abstract: Novel Synthesis of 2,2‐Dialkyl‐3‐dialkylamino‐2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans.

2009

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Benzopyran derivatives R 0350Novel Synthesis of 2,2-Dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans. -The acid-catalyzed three-component reaction involves the retro-aldol formation of formaldehyde. This is confirmed by an analogous synthesis of title compound (XII) via a four-component reaction. -(HUANG, P.-J. J.; CAMERON, T. S.; JHA*, A.; Tetrahedron Lett. 50 (2009) 1, 51-54; Dep. Chem., Acadia Univ., Wolfville, Nova Scotia B4P 2R6, Can.; Eng.) -Mais 14-138

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Novel synthesis of 2,2-dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans

Cited by 27 publications

References 32 publications

Synthetic approaches to 3H‐naphtho[2,1‐b]pyrans and 2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans

Synthetic approaches to 3H‐naphtho[2,1‐b]pyrans and 2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans

Mannich base-connected syntheses mediated by ortho-quinone methides

ChemInform Abstract: Novel Synthesis of 2,2‐Dialkyl‐3‐dialkylamino‐2,3‐dihydro‐1H‐naphtho[2,1‐b]pyrans.

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