A Novel and Facile One-Pot Synthesis of 3-Aryl-4H-benzo[1,4]thiazin-2-amine

Heravi, Majid M.; Baghernejad, Bita; Oskooie, Hossein A.

doi:10.1055/s-0028-1088114

Cited by 14 publications

(6 citation statements)

References 14 publications

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“…It is notable that, at the end of the transformation, the starting isocyanide contributes only one carbon atom in the final molecule (Scheme 13). 25 Interestingly, when o-aminothiophenol (43) was used, no interrupted Ugi products 45 were isolated, as erroneously reported, 26 but a complex mixture of products, one of which was identified as benzo [d]thiazole 44 (Scheme 14). 27…”

Section: Review Syn Thesismentioning

confidence: 89%

Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

et al. 2018

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The formation of the key short-lived intermediate nitrilium ion in the Passerini and Ugi reactions was recognized early in the discovery of these two-multicomponent transformations. Surprisingly, the idea of intramolecularly intercepting it, eluding the attack by the carboxylate, and thus interrupting the normal course of the reaction, was missed by chemists for several decades. In this review we describe, in an exhaustive manner, the reported synthetic approaches, which can be categorized as interrupted Passerini/Ugi reactions. Besides, the clear goal of this review is to show the potential of these transformations, whilst highlighting the underexplored combinations of reagents toward the identification of novel interrupted Passerini/Ugi reactions.1 Introduction2 The Interrupted Ugi Reaction2.1 The Interrupting Functional Group is Present on the Amine Reactant2.2 The Interrupting Functional Group is Present on the Isocyanide Reactant2.3 The Interrupting Functional Group is Present on the Carbonyl Reactant3 The Interrupted Passerini Reaction3.1 The Interrupting Functional Group is Present on the Carbonyl Reactant3.2 The Interrupting Functional Group is Present on the Isocyanide Reactant4 Conclusions and Future Outlook

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Section: Review Syn Thesismentioning

confidence: 89%

Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island

et al. 2018

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“…Our interest to the reaction of o-aminothiophenol has been refueled by a publication 6 reporting on a facile and highyielding preparation of compounds related to 1. According to this article, compound 1 was formed in 89% isolated yield (…”

Section: Scheme 3 Attempted Imcr Of O-aminothiophenolmentioning

confidence: 99%

“…Although in our hands, the outcome of this reaction was similar to the one presented in Scheme 3, we decided to test it under TMSCl-promoted conditions. 2 Scheme 4 Reported preparation of 3-aryl-4H-benzo [1,4]thiazine-2amine 1 6 Simple mixing of o-aminothiophenol an aromatic aldehyde and t-BuNC with TMSCl (1.0 equiv) in methanol and heating the reaction mixture at reflux for 12 hours again provided a complex mixture of products. This was entirely in accordance with the earlier observations made for 1,2-diamines 2 that preformation of an aminal adduct with the carbonyl compound is critical for a successful IMCR.…”

Section: Scheme 3 Attempted Imcr Of O-aminothiophenolmentioning

confidence: 99%

“…However, this attempt only resulted in a complex mixture of products, one of which could be identified as 2, i. e. the products of Ugi reaction involving water 5 as isocyanide-intercepting nucleophile (Scheme 3). Our interest to the reaction of o-aminothiophenol has been refueled by a publication 6 reporting on a facile and high-yielding preparation of compounds related to 1. Simple mixing of o-aminothiophenol an aromatic aldehyde and t-BuNC with TMSCl (1.0 eq.)…”

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confidence: 99%

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o-Aminothiophenol in Reactions with Carbonyl Compounds and Isocyanides: A Word of Caution

Tsirulnikov¹,

Дмитриев²,

Krasavin³

2010

Synlett

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The reaction of o-aminothiophenol with carbonyl compounds and t-BuNC was revisited and was shown to provide 1-(1,3-benzothiazol-3(2H)-yl)methanimines 4 (not described hitherto) and not the earlier reported 4H-benzo[1,4]thiazine 5. To isolate the latter using this reaction a due amount of caution and structure scrutiny is warranted. The basis for assignment of the products to both structural classes is provided.

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“…Polymer-supported reagents/scavengers/linkers are presented in Tables (nonfluorous) and (fluorous). There are 370 libraries and 24 molecular probes extracted from 355 literature citations. − …”

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confidence: 99%